Nitriles-buliding-blocks

On February 16, 1960, Dormael, Andre van; Nys, Jean; Depoorter, Henri published a patent.Synthetic Route of 2510-01-2 The title of the patent was Polymethine dyes containing phosphorus. And the patent contained the following:

Polymethine dyes containing the system: P: C(C: C)nC: are obtained from tri(alkyl or aryl), phosphonium cyclopentadienylides or from the corresponding bisphosphonium compounds by usual polymethine dye reactions. Thus, 2-(β-phenyleniminoethylidene)-3-ethylbenzoselenazoline and triphenylphosphonium cyclopentadienylide (I) give 2-[2-(5-triphenylphosphoranylidene-1-cyclopentadienyl)vinyl]-3-ethylbenzoselenazolium perchlorate, m. 150-51° (EtOH), absorption maximum 522 mμ, and sensitizing an Ag (Cl,Br) emulsion (30 mg. being added per kg. emulsion) to 600 mμ with a maximum at 565 mμ. Similarly, [m.p. (EtOH), absorption maximum (mμ), emulsion, mg. sensitizer, sensitization limit, and maximum (mμ) given]: 2-(β-phenyliminoethylidene)-3-ethyl-5,6-dimethylbenzoxazoline (II) and I give 2-[2-(5-triphenylphosphoranylidene-1-cyclopentadienyl)vinyl]-3-ethyl-5,6-dimethylbenzoxazolinium perchlorate, 284°, 480, AgBr, 30, 565, 520; 2-[β-[N-(p-toluenesulfonyl)anilino]vinyl]-3-ethylbenzothiazolium iodide (III) and I give 2-[2-(5-triphenylphosphoranylidene-1-cyclopentadienyl)vinyl]-3-ethylbenzothiazolium perchlorate, 150° 515, Ag(Cl,Br), 50, 606, 560; 1-methyl-2-methylthioquinolinium methosulfate and I give 1-methyl-2-(5-triphenylphosphoranylidene-1- cyclopentadienyl)quinolinium perchlorate, 192° 445, AgCl, 100, 510, 480; 3-ethyl-5(acetylanilinomethylidene)rhodanine and I give 2-thio-3ethyl-5-(5-triphenylphosphoranylidene-l-cyclopentadienylmethylidene)-2,4-thiazolidinedione, 240° (PrOH), 487, Ag(Cl,Br), 20, 600, 550; I and CH(OEt)3 give 1-triphenylphosphonio-5-(5-triphenylphosphoranylidene-l-cyclopentadienylmethylidene)cyclopentadiene iodide, 249-50o 487, AgBr, 30, 510, -; I and 2-(β-acetylanilinovinyl)-3-ethylthiazolinium bromide give 2-[2-(5-triphenylphosphoranylidene- 1-cyclopentadienyl )vinyl] -3-ethyl-2-thiazolinium perchlorate, 218deg;, 460, AgCl, 30, 520,490; I and 2-thio-3-ethyl5-[2-( 3-ethyl-2-benzothiazolinylidene )-1-benzylethylidene]2,4-thiazolidinedione give 2-(5-triphenylphosphoranylidene1-cyclopentadienyl )-3-ethyl-4-oxo – 5- [2 – (3-ethyl-2-benzothiazolinylidene)-1-benzylethylidene] thiazolinium iodide, 282-3°, 606, Ag(Br,I), 20, 670, 640; I and 4-Me2NC6H4CHO give 1-triphenylphosphonio-5-(p-dimethylaminophenylmethylidene)cyclopentadiene perchlorate, 250°, 495, -, -, -, -; I and 2-methylthio-3-methylbenzothiazolium methosulfate give 2- (5- triphenylphosphoranylidene- 1-cyclopentadienyl)- 3 – methylbenzothiazolium perchlorate, 242°, 398, AgCl, 100, 445, 425; I and 2-methylthio-3-methylthiazolinium iodide give 2-(5-triphenylphosphoranylidene1-cyclopentadienyl)-3-methyl-2-thiazolinium iodide, 210°, 346, -, -, -, -; I and 2-(β-phenyliminoethylidene)-3ethylbenzoxazoline (IV) give 2-[2-(5-triphenylphosphoranylidene-l-cyclopentadienyl)vinyl] – 3 – ethylbenzoxazolium perchlorate, <250°, 480, Ag(Cl,Br), 30, 540, 515; I and 2- (β- methylthio - β - ethylvinyl) - 3 - ethylnaphtho [ 1,2-d] thiazolinium methosulfate give 1-ethyl-2-[2-(5-triphenylphosphoranylidene- 1 -cyclopentadienyl)- 2 - ethylvinyl] naphtho[1,2-d]thiazolium perchlorate, 160°, 542, Ag(Br,I), 30, 625, 580; I and 1-ethyl-2-(β-phenyliminoethylidene)-6methoxy-1,2-dihydroquinoline give 1-ethyl-2-[2-(5-triphenylphosphoranylidene- 1 -cyclopentadienyl)vinyl] -6-methoxyqulnolinium perchlorate, 210°, 550, Ag(Cl,Br), 30, 625, 570; I and -anilinoacrolein anil hydrochloride give 1-triphenylphosphonio-5-[3-(5- triphenylphosphoranylidene-1 cyclopentadienyl)allylidene] cyclopentadiene perchlorate, 244° 597, -, -, -, -; I and glutaconaldehyde dianil hydrochloride give 1-triphenylphosphonio-5-[5-(5-triphenylphosphoranylidene-1-cyclopentadienyl) - 2,4-pentadienylidene] cyclopentadiene perchlorate, <250°, 695, -, -, -, -; I and 1,3-diethyl-2-[β-[N-(p-toluenesulfonyl)anilino]vinyl]5,6-dichlorobenzimidazolium chloride give 1-ethyl-2-[2(5 - triphenylphosphoranylidene-1-cyclopentadienyl)vinyl] 3-ethyl-5,6-dichlorobenzimidazolium iodide, <260°, 482, Ag(Cl,Br), 20, 550, 520; I and anilinomethylidenemalonitrile give 3-(5-triphenylphosphoranylidene-1-cyclopentadienyl)-2-cyano-2-acrylonitrile, 199° (PrOH), 402 -, -, -, -; I, Ac2O, and MeC(OEt)3 give 1-triphenylphosphonio 5-[α-(5-triphenylphosphoranylidene-1-cyclopentadienyl)ethylidene]cyclopentadiene perchlorate, 160°, 488, -, -; II and p-bromophenyldiphenylphosphonium cyclopentadienylide (V) (m. 215°) give 2-[2-[5-(p-bromophenyldiphenylphosphoranylidene)-1-cyclopentadienyl]vinyl]3-ethyl-5,6-dimethylbenzoxazolium perchlorate, 220°, 485, AgBr, 30, 570, 525; III and V give 2-[2-[5-(p-bromophenyldiphenylphosphoranylidene)-1-cyclopentadienyl] vinyl]-3ethylbenzothiazolium perchlorate, -, 519, AgBr, 30, 610, 565; IV and V give 2-[2-[5-(p-bromophenyldiphenylphosphoranylidene)-1-cyclopentadienyl] vinyl]-3-ethylbenzoxazolium perchlorate, -, 478, Ag(Cl,Br), 30, 540, 515; tripropylphosphonium cyclopentadienylide (VI) and II give 2-[2- [ 5-(tripropylphosphoranylidene)-1-cyclopentadienyl] vinyl]-3-ethyl-5,6-dimethylbenzoxazolium perchlorate, -, 487, -, -, -, -; VI and III give 2-[2-[5-(tripropylphosphoranylidene)-1-cyclopentadienyl] vinyl]-3-ethylbenzothiazolium perchlorate. -, 519, -, -, -, -. The experimental process involved the reaction of 2-(2,3-Dihydro-1H-inden-1-ylidene)malononitrile(cas: 2510-01-2).Synthetic Route of 2510-01-2

2-(2,3-Dihydro-1H-inden-1-ylidene)malononitrile(cas:2510-01-2) belongs to nitriles. Some nitriles are manufactured by heating carboxylic acids with ammonia in the presence of catalysts. This process is used to make nitriles from natural fats and oils, the products being used as softening agents in synthetic rubbers, plastics, and textiles and for making amines.Synthetic Route of 2510-01-2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Weiler-Feilchenfeld, Hannah; Agranat, Israel; Bergmann, Ernst D. published an article in 1966, the title of the article was Dipole moments of substituted 1,1-dicyanoethylenes.Application of 2510-01-2 And the article contains the following content:

The dipole moments of a number of 2-substituted 1,1-dicyanoethylenes have been measured. The moments are explained by a combination of 2 effects, partial charge separation and compression of the C(CN)2 angle. From the data obtained with ω,ω-dicyanofulvenes it is concluded that in compounds such as I and II, pseudoarom. structures (such as Ia and IIa contribute to the ground state of the mols. 31 references The experimental process involved the reaction of 2-(2,3-Dihydro-1H-inden-1-ylidene)malononitrile(cas: 2510-01-2).Application of 2510-01-2

2-(2,3-Dihydro-1H-inden-1-ylidene)malononitrile(cas:2510-01-2) belongs to nitriles. Some nitriles are manufactured by heating carboxylic acids with ammonia in the presence of catalysts. This process is used to make nitriles from natural fats and oils, the products being used as softening agents in synthetic rubbers, plastics, and textiles and for making amines.Application of 2510-01-2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Greizerstein, W.; Bonelli, R. A.; Brieux, J. A. published an article in 1962, the title of the article was Polar effects of substituents on the reaction rates of 4-R and 5-R-2-nitrochlorobenzenes with pipefidine in benzene.Formula: C7H3ClN2O2 And the article contains the following content:

The rate constants for the reaction of fourteen 4-Rand of twelve 6-R-2-nitrochlorobenzenes with piperidine in benzene solution were determined The reactions were carried out at constant temperature in sealed tubes each containing 10 ml. benzene solution of the reactants, 0.1M in the halogen compound and 1.0M in piperidine. Cl- was determined by potentiometric titration after addition of 10 ml. 20% HNO3. Rate constants were calculated by means of the equation k2 = {2.303/[t(b – 2a)]} log {a(b – 2x)/b(a – x)}, where a and b were the molar concentrations of the halogen compound and piperidine, rasp., and x the concentration of Cl- at time t. Data from duplicate runs did not differ by more than 1% and rate constants were reproducible within ±2% by independent experiments A spectrophotometric technique was used for compounds having the substituents: 4-NO2, 3-CN, 4-CO2Et, 4-PhN:N, 4-F3C, and 5-CN. The absorption due to the substituted N-phenylpiperidine produced in the reaction was measured at 390420 mμ with a Beckman DU spectrophotometer. Initial concentrations ranged from 10-4 to 10-5M for the halogen compound and piperidine was 102-103 times in excess. Samples were removed from the thermostat, cooled rapidly to room temperature, and the absorbency measured directly. Pseudomonomol. rate constants were calculated graphically from the plot of O.D.∞exptl.-O.D.t; versus t (O.D, = optical d.); second-order rate constants were obtained from these by dividing by the concentration of piperidine. The results were tabulated and showed that in the nucleophilic substitution of these compounds the polarity of the substituted carbon atom was mainly determined by the overall polar effect of the substituent. The reaction followed the Hammett relationship log kR/kH = σ*ρ. Using Jaffe’s σ* values, which are equivalent to Hammett’s σ-constants for most substituents studied, a ρ-value of +3.80 with a correlation coefficient r = 0.934 resulted. For the 4-R-2-nitrochlorobenzenes, alone a ρ-constant of +4.08 with a correlation coefficient of 0.922 was obtained. In order to estimate the mesomeric interaction between a 5-substituent R and the nitro group para to each other, the values of log k2-5R versus σ*meta were introduced into Hammett’s graphic plot of log k2-4R versus σ*4R with ρ = 4.08. From this, the difference between σ*meta values employed and the amended σ-values fitting the exptl. data into the equation log k2-5R = log k2-H + 4.08. σamended was evaluated for each m-substituent. The differences for most substituents were small, but for m-CN, m-CO2Et, and m-Ph the σamended values were smaller than the σ-constants by 0.24, 0.20, and 0.20 units, resp., showing that the activating influence of the nitro group ortho to the site of reaction was roughly constant but smaller than the overall effect in most compounds studied. 4-Chloro-3-nitrobenzotrifluoride and 4-chloro-3-nitroazobenzene showed an inversion of relative reactivity between 35 and 45°, but the order for the more reactive compounds at 45°, k4-No2 > k4-CN > k4-CO2Et > k4-F3C gt; k4-C6H5N2 > k4-CO2H gt; k4-halogen was that expected from their total polar effects upon the site of substitution. The 3-chloro-4-nitrobenzoic acid reacted slower than the p- and o-substituted isomer. The substituents 4-OMe, 4-OEt, and 4-NH2 were found to be deactivating by their mesomeric effect, while halogens produced a marked increase in the rate, specially from the m-position, due to their neg. inductive effect. A Me group in the m-position gave a slight decrease of the rate, this being more pronounced if Me was in the p-position. The phenyl group slightly enhanced the reactivity from the m-positions, a greater increment being observed from the p-position. The experimental process involved the reaction of 3-Chloro-4-nitrobenzonitrile(cas: 34662-29-8).Formula: C7H3ClN2O2

3-Chloro-4-nitrobenzonitrile(cas:34662-29-8) belongs to nitriles. Some nitriles are manufactured by heating carboxylic acids with ammonia in the presence of catalysts. This process is used to make nitriles from natural fats and oils, the products being used as softening agents in synthetic rubbers, plastics, and textiles and for making amines.Formula: C7H3ClN2O2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Campaigne, E.; Subramanya, R.; Maulding, Donald R. published an article in 1963, the title of the article was Ring closure of ylidenemalononitriles. II. Steric effect of a ring at the β position.Synthetic Route of 2510-01-2 And the article contains the following content:

cf. CA 58, 4481b. Heating 1-indanylidenemalononitrile in concentrated sulfuric or polyphosphoric acid yielded the I. Using similar conditions, ring closure of 1-benzosuberylidenemalononitrile to II was effected. Structural assignment on the basis of the infrared and ultraviolet spectra of these and related compounds was given. The experimental process involved the reaction of 2-(2,3-Dihydro-1H-inden-1-ylidene)malononitrile(cas: 2510-01-2).Synthetic Route of 2510-01-2

2-(2,3-Dihydro-1H-inden-1-ylidene)malononitrile(cas:2510-01-2) belongs to nitriles. Some nitriles are manufactured by heating carboxylic acids with ammonia in the presence of catalysts. This process is used to make nitriles from natural fats and oils, the products being used as softening agents in synthetic rubbers, plastics, and textiles and for making amines.Synthetic Route of 2510-01-2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

On April 7, 1965, Brooker, Leslie G. S.; Webster, Frank G. published a patent.SDS of cas: 2510-01-2 The title of the patent was Holopolar cyanine dyes. And the patent contained the following:

Merocyaninelike dyes of structure I and holopolar cyanine dyes (CA 55, 6220b) of structure of II are described. The dyes are useful photog. sensitizers. A mixture of 19.8 g. 2-indanone, 11 g. CH2(CN)2, 2.5 g. NH4OAc, 4 mL. HOAc, and 100 mL. CHCl3 was refluxed 30 min., evaporated to dryness, and the residue washed with H2O and MeOH to give 73% 2-(dicyanomethylene)indan (III), m. 190-3°. Similarly prepared were (compound, m.p., and % yield given): 1-(dicyanomethylene)indan, 147-8°, 65; 1,3diethyl-5-(2-indanylidene)barbituric acid, 165-7°, 47; 1-(dicyanomethylene)-1,2,3,4-tetrahydronaphthalene, 107-8°, 48; 2-(dicyanomethylene)-1,2,3,4-tetrahydronaphthalene, 102-3°, 22; 4-(2-indanylidene)-3-phenylisoxazolin-5-one, 144-5°, 17; 4-(2-indanylidene)-1-phenyl-5-pyrazolone, 273-4°, 71; 3-ethyl-5-(1-indanylidene)rhodanine, 164-6°, 22. A mixture of III 5.4, 2-(acetanilidovinyl)-3-ethylbenzothiazolium iodide (IV) 13.5, Et3N 3.3 g., and 50 mL. EtOH was refluxed 15 min. and cooled. The precipitate was extracted with hot MeOH and recrystallized from pyridine-MeOH to give 21% I [X = S, Y = C(CN)2, R = Et, R’ = H, n = 0, m = p = 1] (V),m. 246-50° (decomposition). A mixture of V 1.98, IV 2.25, Et3N 0.6 g., and 15 mL. pyridine was refluxed 10 min. and cooled. The precipitate was extracted with two 350-mL. portions of hot pyridine to give 33% II [X = Z = S, Y = C(CN)2, R = R’ = Et, p = q = 1], m. 288-9°, sensitivity maximum 690 mμ, sensitivity limit 780 mμ. Similarly prepared I and II are tabulated. Formula,X,Y,Z,R,R1,Ar,Ar1,n,m,p,q,%yield,m.p.(decomposition),sensitivity maximum(mμ),sensitivity limit(mμ);I,S,C(CN)2, ,Me, , , ,1,0,0, ,35,245-6°,545,565;I,S,C(CN)2, ,Et,H, , ,1,0,1, , ,259-60°,660,680;I,S,C(CN)2, ,Et,H, , ,1,0,2, ,36,240-1°, , ;I,O,C(CN)2, ,Me, , , ,1,0,0, ,28,230-1°,490,510;I,S,C(CN)2, ,Me, ,benzo, ,1,0,0, ,55,265-7°,550,575;I,CH:CH:,C(CN)2, ,Et, , , ,1,0,0, ,19,227-8°, , ;I,S,C(CN)2, ,Et,Me,benzo, ,1,0,1, ,1,191-3°, , ;I,S,C(CN)2, ,Et, , , ,0,1,0, ,46,256-8°, , ;I,S,C(CN)2,Et,H, , ,0,1,2, ,22,228-30°, , ;I,O,C(CN)2, ,Et,H, , ,0,1,1, ,28,214-15°, , ;I,S,A, ,Me, , , ,0,1,0, ,12,272-3°, , ;I,S,C(CN)2, ,Me, , , ,2,0,0, ,76,232-3°, ,555;I,S,C(CN)2, ,Me, ,benzo, ,2,0,0, ,80,289-90°,555,580; I,CH:CH,C(CN)2, ,Et, , , ,2,0,0, ,33,285-6°, , ;I,O,C(CN)2, ,Et,H, , ,2,0,1, ,19,213-14°,600,690;I,S,C(CN)2, ,Me,H, , ,2,0,1, ,5,231-2°,580,690;I,O,B, ,Et,H, , ,1,0,1, ,4,192-7°, , ;I,S,B, ,Et,H,benzo, ,1,0,1, ,8,169-70°, , ;I,S,C(CM)2, ,Et, , , ,1,1,0, ,54,254-6°, , ;I,S,C(CN)2, ,Et, ,benzo, ,1,1,0, ,4,222-5°, , ;I,S,C(CN)2, ,Et,H, , ,1,1,1, ,8,218-25°, , ;II,S,C(CN)2,S,Et,Et, , , , ,2,2,13,237-8°,630,690;II,S,C(CN)2,S,Et,Et, , , , ,1,2,35,244-5°,810,840;II,O,C(CN)2,S,Et,Et, , , , ,1,1,45,255-6°,685,730;II,S,A,S,Me,Et, , , , ,0,2,27,285-6°,730,810;II,S,A,S,Me,Me, , , , ,0,0,28,>310°, , ;II,S,A,S,Et,Et, , , , ,1,1,61,>310°,750,770;II,O,A,O,Et,Et, , , , ,1,1,41,280-1°,680,720;II,S,A,S,Me,Me,benzo,benzo, , ,0,0,62,241-3°,590,620;II,S,C(CN)2,S,Me,Me, , , , ,0,0,32,>310,565,610;II,S,A,S,Me,Me, ,benzo, , ,0,0,54,231-2°,555,575; The experimental process involved the reaction of 2-(2,3-Dihydro-1H-inden-1-ylidene)malononitrile(cas: 2510-01-2).SDS of cas: 2510-01-2

2-(2,3-Dihydro-1H-inden-1-ylidene)malononitrile(cas:2510-01-2) belongs to nitriles. Some nitriles are manufactured by heating carboxylic acids with ammonia in the presence of catalysts. This process is used to make nitriles from natural fats and oils, the products being used as softening agents in synthetic rubbers, plastics, and textiles and for making amines.SDS of cas: 2510-01-2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Govindachari, T. R.; Rajappa, S.; Sudarsanam, V. published an article in 1963, the title of the article was A synthesis of ellipticine.Application In Synthesis of 3-Amino-2,5-dimethylbenzonitrile And the article contains the following content:

2,5-Dimethyl-4-nitrobenzoic acid (4.5 g.) was converted into the Et ester [by refluxing in 70 ml. absolute EtOH containing 8 ml. H2SO4 (d. 1.84) 6 hrs.] (4 g.), b0.1 120-3°, which was reduced catalytically (30 lb./in.2 H, Adams catalyst; 1.5 hrs., room temperature) to Et 4-amino-2,5-dimethylbenzoate (I), m. 78-80° (C6H6-petr. ether). I on diazotization followed by SnCl2 reduction afforded Et 4-hydrazino-2,5-dimethylbenzoate (II), m. 135-6° (C6H6-petr. ether). A mixture of 1.1 g. II, 0.6 g. cyclohexanone (III), 15 ml. EtOH, and 2 ml. HCl (d. 1.16) was refluxed (steam-bath, 4 hrs.) and poured into 100 ml. H2O to give 0.8 g. Et 1,2,3,4-tetrahydro-5,8-dimethylcarbazole-6-carboxylate (IV) (washed, dried and sublimed at 170-80°/0.001 mm.), m. 157-9° (C6H66-petr. ether). IV (0.5 g.) in 10 ml. Decalin was heated (220°, 2 hrs.) with Pd-C (5%, 0.5 g.), the mixture filtered, catalyst washed with Me2CO, and the combined filtrates evaporated in vacuo. Chromatography of the residue in C6H6 over Al2O3 (basic Al2O3 of Riedel deHahn was used throughout) afforded 0.17 g. Et 1,4-dimethylcarbazole-3-carboxylate (V), m. 150-2° (C6H6-petr. ether); λ 245, 275, 310, 335 mμ (log ε 4.45, 4.56, 3.82, 3.44). V (1 g.) in 50 ml. dry ether was added to a suspension of 0.5 g. LiAlH4 in dry ether with stirring, the mixture stirred 2 hrs., decomposed (moist ether-H2O), and the organic phase dried and distilled to give 0.6g, 1,3,4-trimethylcarbazole (VI), m. 145-6° (C6H6-petr. ether). Its structure was indicated by infrared (IR) spectrum [only a single sharp band at 2.8 μ (NH)], analysis, and by the recovery of VI after treatment with Ac2O and C5H5N. 2-Cyano-5-nitro-p-xylene on reduction (30 lb./in.2 H; Pd-C; room temperature, 1 hr.) gave 5-amino-2-cyano-p-xylene (VII), m. 158-60° (C6H6); Ac derivative m. 190-2° (MeOH). Diazotization of VII followed by SnCl2 reduction afforded 2-cyano5-hydrazino-p-xylene, m. 161-3° (MeOH), which on condensation with III (as for IV) gave 6-cyano-1,2,3,4-tetrahydro-5,8-dimethylcarbazole (VIII), m. 270-3° (Me2CO), λ 248, 280 mμ (log ε 4.94, 3.88). Dehydrogenation (Pd-C) of VIII yielded 3-cyano-1,4-dimethylcarbazole (IX), m. 249-51° (Me2CO), λ 245, 270, 320, 335 mμ (log ε 4.59, 4.68, 3.56, 3.46). IX (0.4 g.), 30 ml. ethylene glycol and 10 g. KOH in 10 ml. H2O was refluxed 20 hrs., poured into 100 ml. H2O, filtered, the filtrate acidified (HCl) and extracted with EtOAc, and the extract washed (H2O), dried, and distilled to give 0.1 g. 1,4-dimethylcarbazole-3-carboxylic acid (X), m. 253-5° (Me2CO). IX (0.5 g.) in 100 ml. MeOH and 5 g. KOH in 5 ml. H2O was shaken 6 hrs. at room temperature with H (40 lb./in.2) (Raney Ni) and MeOH was removed from the filtered solution to give 0.4 g. 3-aminomethyl-1,4-dimethylcarbazole (XI), m. 210-12°. The Schiff base obtained by condensation of XI with glyoxal semi-diethyl acetal could not be cyclized to ellipticine (XII). Alternatively, 3,6-dimethyl-2-nitrobenzaldehyde was converted into its oxime, which on dehydration (Ac2O) yielded 2-cyano-3-nitro-p-xylene (XIII), m. 85° (C6H6-petr. ether); ν 4.5 μ (CN). XIII on reduction (25 lb./in.2 H; Pd-C) gave 3-amino-2-cyano-p-xylene (XIV), b0.3 106-8°; ν 2.75, 2.85 μ (NH2) and 4.5 μ (CN); acetate m. 74-5° (C6H6-petr. ether). A suspension of 8.4 g. XIV in 40 ml. HCl (d. 1.7) and 18 ml. H2O was diazotized (0°) with NaNO2 (4.3 g. in 15 ml. H2O), the solution added dropwise with stirring to a solution of 12 g. CuCl2 in 50 ml. HCl (d. 1.17) at 0°, the solution allowed to warm to room. temperature left overnight, heated (60°), cooled, extracted with ether, and the extract washed with dilute HCl, H2O, dilute NaOH solution and again with H2O, dried, and evaporated Removal in vacuo yielded 8.3 g. 3-chloro-2-cyano-p-xylene (XV), b0.3 84-6°, m. 72-4° (petr. ether); ν 4.5 μ (CN). KNO3 (2.5 g.) in 35 ml. H2SO4 (d. 1.84) at 0° was added with stirring to 4 g. XV in 25 ml. H2SO4 (d. 1.84), and the mixture stirred 2 hrs. at 5° and poured onto crushed ice to give 4.1 g. 2-chloro-3-cyano-5-nitro-p-xylene (XVI), m. 86-8° (aqueous EtOH). Pd-CaCO3 (5%; 2 g.) was shaken with H (10 lb./in.2, 10 min.). A solution of 2 g. XVI in 100 ml. EtOH and 20 g. NH4Ac was then added and the whole shaken with H (30 lb./in2., 1 hr.); EtOH removed from the filtrate, the residue diluted with H2O, extracted with ether, and the extract washed with NaHCO3 and H2O, dried, and distilled; the residue was sublimed (140°/0.01 mm.) to give 1 g. 2-amino-6-cyano-p-xylene (XVII), m. 118-20° (C6H6-petr. ether); ν 2.85 (NH2) and 4.5 μ (CN). Diazotization of XVII followed by SnCl2 reduction afforded 6-cyano-2-hydrazino-p-xylene (XVIII), m. 173-5° (MeOH). Refluxing 1.4 g. XVIII, 1 g. III, 20 ml. EtOH, and 6 ml. HCl (d. 1.17) gave 0.9 g. 7-cyano-1,2,3,4-tetrahydro-5,8-dimethylcarbazole (XIX), m. 229-31° (EtOH); ν 2.9 (NH) and 4.5 μ (CN), λ 228,250,295, 330 mμ (log ε 4.43, 4.45, 4.04, 4.05); it gave unsatisfactory C analytical values. XIX (1.3 g.) on refluxing with aqueous KOH (5 g. in 5 ml. H2O) and 80 ml. ethylene glycol (as for X) gave 1.3 g. 1,2,3,4-tetrahydro-5,8-dimethylcarbazole-7-carboxylic acid (XX), m. 241° (decomposition) (MeOHC6H6), which with EtOH saturated with HCl gave the Et ester (XXI), m. 137-41° (C6H6-petr. ether); ν 2.85 (NH) and 5.9 μ (CO2Et). XXI on heating (210°, 15 hrs.) with 5% Pd-C in a CO2 atm. gave 0.6 g. Et 1,4-dimethylcarbazole-2-carboxylate (XXII), m. 118-20° (C6H6-petr. ether), λ 250, 305, 350 mμ (log ε 4.69, 4.33, 3.7). Esterification (CH2N2 in ether) of XX gave Me 1,2,3,4-tetrahydro-5,8-dimethylcarbazole-7-carboxylate, m. 158-60° (C6H6), which on heating in Decalin (200°, 15 hrs.) with Pd-C gave Me 1,4-dimethylcarbazole-2-carboxylate (XXIII), m. 150-2° (C6H6-petr. ether), ν 2.9 (NH) and 5.85 μ (CO2Me). XXIII (1 g.) on refluxing (steam-bath, 2 hrs.) with KOH (2.5 g. in 2 ml. H2O) and working up as usual gave 0.8 g. 1,4-dimethylcarbazole-2-carboxylic acid, m. 238-40° (Me2CO). LiAlH4 reduction (as in VI) of XXIII (in tetrahydrofuran) gave 2-hydroxymethyl-1,4-dimethylcarbazole (XXIV), m. 146-8° (C6H6), ν 2.7 (OH) and 2.8 μ (NH). Oxidation of XXIV with C5H5N-Cr2O3 (0°, stirred 30 min., left at room temperature 20 hrs.) gave 1,4-dimethylcarbazole-2-aldehyde (XXV), m. 201-3° (MeOH-C6H6), ν 2.9 (NH) and 5.95 μ (CHO). XXV (0.9 g.) in 30 ml. HOAc was refluxed 2 hrs. with 3 ml. MeNO2 and 1 g. NH4Ac; the mixture on pouring into H2O gave 0.9 g. 1,4-dimethyl-2-(2-nitrovinyl)carbazole (XXVI), m. 273-5° (decomposition) (EtOAc). Reduction of XXVI with LiAlH4 afforded 2-hydroxymethyl-1,4-dimethylcarbazole (XXVII), m. 196-8° (MeOH-C6H6). XXVII (0.5 g.) was heated with 20 ml. HCO2Et in a sealed tube (120°, 6.5 hrs.), excess HCO2Et distilled, and the residue chromatographed on Al2O3 to give 0.15 g. 2-(2-formamidoethyl)-1,4-dimethylcarbazole (XXVIII), m. 183-5° (MeOH-C6H6); ν 2.85 (NH) and 5.95 μ (NHCHO). XXVIII (0.15 g.) was cyclized by refluxing (150°, 0.5 hr.) with 5 ml. POCl3 in 130 ml. dry xylene, xylene was removed in vacuo, the residue extracted with hot dilute HCl, the filtered acid extract was basified (K2CO3), extracted with CHCl3, and the extract washed (H2O), dried (Na2SO4), and distilled to give 30 mg. 3,4-dihydro-5,11-dimethyl-6H-pyrido[4,3-b]carbazole (XXIX) (1,2-dihydroellipticine), m. 292-6°, identical with an authentic sample (Buchi, et al., CA 56, 11631f) in IR ultraviolet (UV), m. p. and mixed m. p., and Rf(1: 1 EtOH-C6H6) values. Dehydrogenation of 30 mg. XXIX with Pd-C (5%; 50 mg.) in Decalin (220°, 3 hrs., CO2 atm.) gave 5 mg. XII, m. 310-14° (decomposition) (EtOAc), identical with an authentic sample (Goodwin, et al., CA 53, 22046f) (m. p., mixed m. p., IR and UV spectra). XII was also synthesized recently by Cranwell and Saxton (CA 57, 3499a; 59,681e) by a different route. The experimental process involved the reaction of 3-Amino-2,5-dimethylbenzonitrile(cas: 90557-28-1).Application In Synthesis of 3-Amino-2,5-dimethylbenzonitrile

3-Amino-2,5-dimethylbenzonitrile(cas:90557-28-1) belongs to nitriles. Some nitriles are manufactured by heating carboxylic acids with ammonia in the presence of catalysts. This process is used to make nitriles from natural fats and oils, the products being used as softening agents in synthetic rubbers, plastics, and textiles and for making amines.Application In Synthesis of 3-Amino-2,5-dimethylbenzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

On September 2, 1960, there was a patent about color photography.Quality Control of 2-(2,3-Dihydro-1H-inden-1-ylidene)malononitrile The title of the patent was Cyanines for color photography. And the patent contained the following:

1-Dicyanomethyleneindan (I), m. 147-8o (MeOH), was prepared in 65% yield as grayish white crystals by refluxing 39.6 g. 1-indanone, 19.8 g. malononitrile, 2.5 g. NH4OAc, 4 cc. AcOH, 40 cc. CHCl3, and simultaneous distillation of 5.4 cc. H2O. 2-Dicyanomethyl- eneindan, m. 190-3, was prepared in 73% yield (brownish), 1-dicyanomethylene-1,2,3,4-tetrahydronaphthalene (colorless), m. 107-8 (EtOH), in 48% yield from 1-tetralone, and 2-dicyanomethylene-1,2,3,4-tetrahydronaphthalene (colorless), m. 102-3 (MeOH), in 22% yield. 1,3-Diethyl-5-(2indanylidene)barbituric acid (colorless), m. 165-7 (EtOH) was prepared in 47% yield by refluxing for 2 h. 19 g. 2-indanone, 26.5 g. 1,3-diethylbarbituric acid, and 2.5 cc. piperidine in 100 cc. EtOH. 1-Dicyanomethylene-2-(3methyl-2-benzothiazolinylidene)indan (orange), m. 245-6 (decomposition) (pyridine/MeOH), was prepared in 35% yield by refluxing for 15 min. 5.4 g. I, 7.4 g. 3-methyl-2-methylthiobenzothiazolium p-toluenesulfonate, 6.06 g. Et3N, 50 cc. EtOH; it sensitized Ag(Br,I) emulsions to 565 mμ, maximum 545 mμ. Similarly were obtained (m.p., % yield, limit and absorption maximum in mμ given): 1-dicyanomethylene-2-(3-ethyl2-benzothiazolinylideneethylidene)indan (green needles), 259-60 (decomposition), -, 680, 660; 1-dicyanomethylene-2[(3 – Et – 2- benzothiazolinylidene) – 2- butenylidene]indan (dark green), 240-1 (decomposition), 36, -, -; 1-dicyanomethylene- 2- (3- methyl-2- benzoxazolinylidene)indan (brownish red ), 230-1 ( decomposition ), -, 510, 490; 1-dicyanomethylene2- ( 1 – methylnaphtho [ 1,2] thiazolin-2- ylidene)indan (red), 265-7 (decomposition), 55, 575, 550; 1-dicyanomethylene-2-(1ethyl-2(1H)-quinolylidene)indan, 227-8 (decomposition), 19, -,-; 1-dicyanomethylene-2-[(1-ethylnaphtho[1,2]thiazolin-2-ylidene)isopropylidene]indan (dark), 191-3 (decomposition), 1, -, -; 2-dicyanomethylene-1-[(3-ethyl-2benzothiazolinylidene)ethylidene]indan (II) (green), 246-50 (decomposition), 21, -, -; 2-dicyanomethylene-1-[(3ethyl-2-benzothiazolinylidene)-2-butenylidene]indan (dark green), 228-30, 22, -, -; 2-dicyanomethylene-1-[(3ethyl-2-benzoxazolinylidene)ethylidene]indan (green), 2145 (decomposition), 28, -, -; 2-dicyanomethylene-1,3-bis(3methyl-2-benzothiazolinylidene )indan (dark needles), <310, 32, 610, 565; 2-dicyanomethylene-1,3-bis[(3-ethyl2-benzothiazollnylidene)ethylidene]indan (dark green), 2889, 33, 780, 690; 2-dicyanomethylene-1,3-bis[(3-ethyl-2benzothiazolinylidene)-2-butenylidene]indan (dark), 2378 (decomposition), 13, 690, 630; 2-dicyanomethylene-1-[(3ethyl-2-benzothiazolinylidene )-2- butenylidene] - 3- [( 3- ethy-2-benzothiazolinylidene)ethylidene]indan (black), 244-5 (decomposition), 35, 840, 810; 2-dicyanomethylene-1-[(3-ethyl2-benzothiazolinylidene)ethylidene]-3- [(3-ethyl-2-benzoxazolinylidene)ethylidene]indan (gray), 255-6° (decomposition), 45,730,685; 1,3-diethyl-5-[1-(3-methyl-2-benzothiazolinylidene)indan-2-ylidene] barbituric acid (brownish red), 272-3 (decomposition) (pyridine), 12, -, -; 1,3-diethyl-5-[1,3-bis(3-methyl- 2- benzothiazolinylidene)indan-2-ylidene] barbituric acid (red), <310, 28, -, -; 1,3-diethyl-5-[1,3-bis(3ethyl - 2 - benzothiazolinylideneethylidene)indan - 2 - ylidene] barbituric acid (green), <310, 61, 770, 750; corresponding benzoxazolinylidene derivative (green), 280-1 (decomposition), 41, 720, 680; 1,3-diethyl-5-[1,3-bis(methylnaphtho [ 1,2] thiazolin-2-ylidene )indan-2-ylidene] barbituric acid (dark), 242-3, 62, 620, 590; 1,3-diethyl-5-[1-(3-ethyl-2benzothiazolinylidene)-2-butadienylidene] -3-(3-methyl-2- benzothiazolinylidene )indan-2-ylidene] barbituric acid (green), 285-43 (decomposition), 27, 810, 730; 1,3-diethyl-5-[1- (3 - methyl- 2- benzothiazolinylidene)- 3- ( 1 -methylnaphtho- [1,2]thiazolinylidene)indan-2-ylidene]barbituric acid (red), 231-2 (decomposition), 54, 575, 555; 1-dicyanomethylene- 1,2,3,4- tetrahydro- 2- (3-methyl- 2- benzothiazolinylidene)- naphthalene (red), 232-3 (decomposition), 76, 555, -; 1-di- cyanomethylene- 1,2,3,4- tetrahydro-2- (1-methylnaphtho- [1,2]thiazolin-2-ylidene)naphthalene (brownish red), 289- 90 (decomposition), 80, 580, 555; 1-dicyanomethylene-2-(1- ethyl-2(1H)-quinolylidene)- 1,2,3,4-tetrahydronaphthalene (red), 285-6 (decomposition), 33, -, -; 1-dicyanomethylene- 2-[(3-ethyl-2-benzoxazolinylidene)ethylidene]- 1,2,3,4-tetra- hydronaphthalene (green needles), 213-14 (decomposition), 19, 690, 600; and 1-dicyanomethylene-1,2,3,4-tetrahydro-2-[(3-methyl-2-benzothiazolinylidene)ethylidene] naphthalene (green needles), 231-2 ( decomposition ), 5, 690, 580. The experimental process involved the reaction of 2-(2,3-Dihydro-1H-inden-1-ylidene)malononitrile(cas: 2510-01-2).Quality Control of 2-(2,3-Dihydro-1H-inden-1-ylidene)malononitrile

2-(2,3-Dihydro-1H-inden-1-ylidene)malononitrile(cas:2510-01-2) belongs to nitriles. Some nitriles are manufactured by heating carboxylic acids with ammonia in the presence of catalysts. This process is used to make nitriles from natural fats and oils, the products being used as softening agents in synthetic rubbers, plastics, and textiles and for making amines.Quality Control of 2-(2,3-Dihydro-1H-inden-1-ylidene)malononitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Fox, Kenneth; Turner, J. E. published an article in 1966, the title of the article was W.K.B. treatment of bound states in an electric-dipole potential.Safety of 2-(2,3-Dihydro-1H-inden-1-ylidene)malononitrile And the article contains the following content:

The W.K.B. (Wentzel-Kramers-Brillouin) method is applied to the problem of bound states of an electron in the field of a finite dipole. A necessary condition for binding is derived which suggests that bound states may exist only if the dipole moment is larger than a certain min. value. The number of bound states given by the W.K.B. method is comparable to the exact number for the 1- and 3-dimensional sq.-well potentials. The experimental process involved the reaction of 2-(2,3-Dihydro-1H-inden-1-ylidene)malononitrile(cas: 2510-01-2).Safety of 2-(2,3-Dihydro-1H-inden-1-ylidene)malononitrile

2-(2,3-Dihydro-1H-inden-1-ylidene)malononitrile(cas:2510-01-2) belongs to nitriles. Some nitriles are manufactured by heating carboxylic acids with ammonia in the presence of catalysts. This process is used to make nitriles from natural fats and oils, the products being used as softening agents in synthetic rubbers, plastics, and textiles and for making amines.Safety of 2-(2,3-Dihydro-1H-inden-1-ylidene)malononitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

On October 31, 1957, there was a patent about photographic paper, photography.Name: 2-(2,3-Dihydro-1H-inden-1-ylidene)malononitrile The title of the patent was Photographic emulsions. And the patent contained the following:

The emulsion consists of a mixture of nontanned gelatin, a Ag halide, a tanning or nontanning developer, and a stabilizer. The latter is chosen from 5,5-dimethyl-1,3-cyclohexanedione (I), oxalyl dihydrazone of cyclohexanone (II), 4-cyano-5-phenyl-1,3-cyclohexanedione (III), 5-phenyl-1,3-cyclohexanedione (IV), dicyanomethylenecyclohexane, 1-dicyanomethylene-1,2,3,4-tetrahydronaphthalene, 2-methyl-1-phenyl-4,6-(1H,5H)-pyrimidinedione, dicyanomethyleneindan, (1-cyano-1-ethoxycarbonylmethylene)cyclopentane, cyclohexanone oxime, 2,4-pentanedione dioxime, and 2,5-hexanedione dioxime. I, II, III, and IV also prevent tanning during aging. For example, a contrasting AgCl emulsion (1 mole AgCl in 340 g. gelatin) was melted at 40°; 200 g. aqueous 15% saponin solution and 5 g. dimedon in 50 cc. MeOH were added. A solution of 45 g. 4-phenylpyrocatechol and 19.3 g. 4-methoxy-naphthol in 129 g. tritolyl phosphate at 80° was poured in a stirred solution containing 64.3 g. gelatin, 64 g. aqueous 8% saponin solution and 579 cc. H2O at 50°. The dispersion thus obtained was added to the previous emulsion. The mixture was coated on 46 sq. m. nontanned gelatinized paper. The experimental process involved the reaction of 2-(2,3-Dihydro-1H-inden-1-ylidene)malononitrile(cas: 2510-01-2).Name: 2-(2,3-Dihydro-1H-inden-1-ylidene)malononitrile

2-(2,3-Dihydro-1H-inden-1-ylidene)malononitrile(cas:2510-01-2) belongs to nitriles. Some nitriles are manufactured by heating carboxylic acids with ammonia in the presence of catalysts. This process is used to make nitriles from natural fats and oils, the products being used as softening agents in synthetic rubbers, plastics, and textiles and for making amines.Name: 2-(2,3-Dihydro-1H-inden-1-ylidene)malononitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts