Author: Jessica.F

Some common heterocyclic compound, 38487-86-4, name is 2-Amino-4-chlorobenzonitrile, molecular formula is C7H5ClN2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. SDS of cas: 38487-86-4

Method 2 (from 3-ethylacetate-2-oxa-l-adamantyl methanesulfonate (3))A suspension of anhydrous A1C13 (417 mg, 3.13 mmol) and mesylate (3) (830 mg, 2.6 mmol) in dry 1 ,2-dichloroethane (4 mL) was stirred at reflux. The reaction mixture became orange and exothermic. After 5 minutes, a suspension of 4-chloro-2-aminobenzonitrile (438 mg, 2.87 mmol) in dry 1 ,2-dichloroethane (5 mL) was added dropwise to the refluxing mixture and the reflux was maintained for 8h. The reaction mixture was then cooled to r. , diluted with water (10 mL) and THF (10 mL), basified by addition of 5 M NaOH solution (10 mL) and stirred at r.t. for 30 min. The phases were separated (DCM was added if necessary) and the aqueous layer was extracted with AcOEt (3 x 20 mL). The combined organic layers were dried with Na2S04 and concentrated under reduced pressure to afford a yellow solid. Purification by flash chromatography (cyclohexane / AcOEt 10/0 to AcOEt / MeOH 9/1, v/v) afforded a pale yellow solid. Recrystallisation from petroleum ether / AcOEt, 8/2, v/v afforded the desired Huprine (HUP 1) as a white solid (799 mg, 88%).Rf (AcOEt / MeOH 9/1, v/v) = 0.33.m.p. = 179-180C.IR (KBr): v = 3352, 3209, 2929, 1727, 1648, 1609 ,1559, 1490, 1426, 1371, 1308, 1285, 1258, 1154, 1031, 929 cm”1.1H NMR (300 MHz, CDC13): delta = 0.99 (t, J = 7.2 Hz, 3H, ¾), 1.88-1.93 (m, 1H, H10), 2.02-2.08 (m, 2H, ¾<>, ¾), 2.57 (dd, J = 17.1 Hz, J = 3.9 Hz, 1H, ¾), 2.70-2.74 (m, 1H, H7), 2.72-2.77 (m, 2H, ¾), 2.94 (d, J= 17.7 Hz, 1H, H6), 3.11 (dd, J= 17.5 Hz, J = 5.5 Hz, 1H, H6), 3.16-3.20 (m, 1H, H?), 3.92 (q, J = 7.1 Hz, 2H, Hi7), 5.05 (brs, 2H, NH2), 5.67 (d, J= 5.1 Hz, 1H, H8), 7.21 (dd, J= 9.0 Hz, J = 1.9 Hz, 1H, H2), 7.65 (d, J= 9.0 Hz, 1H, Hi), 7.81 (d, J= 1.9 Hz, 1H, H4).13C NMR (75 MHz, CDC13): delta = 14.0 (Ci8), 27.4 (Cn), 28.4 (C7), 28.8 (C10), 33.9 (C13), 39.2 (C6), 43.3 (CM), 60.6 (C17), 114.9 (Cl la or C12a), 115.8 (Cl la or C12a), 121.9 (Ci), 124.7 (C2), 127.1 (C4), 129.5 (C8), 129.8 (C9), 134.6 (C3), 146.4 (C4a or C12), 146.9 (C4aor C12), 158.1 (C5a), 171.5 (C15).MS (ESI+): m/z (%): 357.33 (100) [M+H]+, 359.20 (36). ICso rh-AC E : 3.90 +/- 0.50 iiM.ICso r/i-BuChE : 137 +/- 1 1 iiM.ICso erythrocyte /i-AChE : 38.3 iiM.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 38487-86-4, its application will become more common.

Reference:
Patent; UNIVERSITE DE ROUEN; RONCO, Cyril; RENARD, Pierre Yves; JEAN, Ludovic; NACHON, Florian; ROMIEU, Anthony; WO2011/124712; (2011); A1;,
Nitrile – Wikipedia,
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Synthetic Route of 78473-00-4, The chemical industry reduces the impact on the environment during synthesis 78473-00-4, name is 4-Amino-3,5-dichlorobenzonitrile, I believe this compound will play a more active role in future production and life.

EXAMPLE 21 7-Difluoromethoxy-2-ethylfuro[2,3-c]pyridine-4-carboxylic acid (2,6-dichloro-4-cyanophenyl)amide Starting from 7-difluromethoxy-2-ethylfuro[2,3-c]pyridine-4-carboxylic acid 4-nitrophenyl ester (100 mg) and 4-amino-3,5-dichlorobenzonitrile (99 mg). Purification by column chromatography on silica eluding with 1% methanol in dichloromethane afforded the title compound as a white solid (12 mg). TLC Rf 0.65 (2.5% methanol in dichloromethane) m.p. 208-210 C.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 4-Amino-3,5-dichlorobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Darwin Discovery, Ltd.; US6169090; (2001); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 140860-51-1,Some common heterocyclic compound, 140860-51-1, name is 2-Bromo-4-methoxybenzonitrile, molecular formula is C8H6BrNO, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Step b. To a stirred solution of tert-butyl 6-(methylsulfonamido)-4-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)isoindoline-2-carboxylate (1.030 g, 2.37 mmol) in l,4-dioxane:water (9: 1, 5 ml) were added K2C03 (0.300 g, 2.37 mmol) and 2-bromo-4-methoxybenzonitrile (CAS Number 140860- 51-1; 0.250 g, 1.185 mmol) at rt. The reaction mixture was degassed for 20 min before addition of PdCl2(dppf) (0.087 g, 0.118 mmol). The resulting reaction mixture was heated at 90C for 2 h. The reaction mixture was cooled to rt, poured into water (50 ml) and extracted with EtOAc (2 x 50 ml). The combined organic phase washed with brine (40 ml), dried over Na2S04, filtered and concentrated under reduced pressure. The residue was purified by flash column chromatography (8 % EtOAc in hexane) yielding tert-butyl 4-(2-cyano-5-methoxyphenyl)-6-(methylsulfonamido)isoindoline-2- carboxylate (0.150 g, 0.338 mmol). LCMS: Method A, 2.038 min, MS: ES+ 444.6; NMR (400 MHz, DMSO-d6) delta ppm 9.99 (s, 1H), 7.89 (t, J= 6.0 Hz, 1H), 7.23 – 7.10 (m, 4 H), 4.64 (d, J=11.2, 2 H), 4.42 (d, J=10.4, 2 H), 3.85 (s, 3 H), 3.02 (s, 3 H), 1.40 (d, J=15.6 Hz, 9 H).

The synthetic route of 140860-51-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MISSION THERAPEUTICS LIMITED; GIBSON, Karl Richard; JONES, Alison; KEMP, Mark Ian; MADIN, Andrew; STOCKLEY, Martin Lee; WHITLOCK, Gavin Alistair; WOODROW, Michael D; (241 pag.)WO2017/158388; (2017); A1;,
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Related Products of 21423-81-4,Some common heterocyclic compound, 21423-81-4, name is 3-Chloro-4-methylbenzonitrile, molecular formula is C8H6ClN, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Example 53 3- {5-[4-(6-Methoxy-pyridin-3-yl)-5-methyl-4H-[1,2,4]triazol-3-yl]-pyra zin-2-yl} -4-methyl-benzonitrile A mixture of 3-chloro-4-methylbenzonitrile (1g, 6. 6mmol), bis (PINACOLATO) DIBORON (1. 8G,. 7. 0MMOL), caesium carbonate (6. 4g, 19. 8MMOI) and the product of . preparation 3 (5mg, cat) in 1,4-dioxan (50mL) was heated under reflux for 4 hours. The reaction mixture was then cooled TO ROOM TEMPERATURE, FILTERED through CELITENo. AND CONCENTRATED IN VACUO. A portion of the residue (145mg, 0. 6MMOL), the product of preparation 30 (90MG, 0. 3MMOL), caesium carbonate (293mg, 0. 9mmol) and the product of preparation 3 (2mg, cat) were then dissolved in 1,4-dioxan and the mixture was heated under reflux for 18 hours. The mixture was then cooled to room temperature, filtered through Celiez and concentrated IN VACUO. Purification of the residue by . column chromatography on silica gel, eluting with dichloromethane : methanol, 100: 0 to 97: 3, afforded the title compound as a white solid in 3% yield, 3mg. HNMR (CDCl3, 400MHZ) 5 : 2.41 (s, 3H), 2.46 (s, 3H), 4.02 (s, 3H), 6.90 (d, 1H), 7.43 (d, 1H), 7.53 (DD, 1H), 7.63 (dd, 1H), 7. 70 (d, 1H), 8. 09 (d, 1H), 8.41 (d, 1H), 9. 55 (D, 1 H). MS APCI+ m/z 383 [MH] +

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Chloro-4-methylbenzonitrile, its application will become more common.

Reference:
Patent; PFIZER LIMITED; PFIZER INC.; WO2005/28452; (2005); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 403-54-3,Some common heterocyclic compound, 403-54-3, name is 3-Fluorobenzonitrile, molecular formula is C7H4FN, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: Benzonitrile 1a (1 mmol), Na2S*9H2O (1.2 mmol) and DMF (1 mL) were added into a 10 mL bottle. The reactor was placed in a heating magnetic stirrer at 130 C. After 2.5 h, by adding about 3 mL H2O after the reaction to disperse the solid product, the reaction mixture was extracted with EtOAc (3 x 3 mL), and the mixture was purified by column chromatography.

The synthetic route of 403-54-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Cao, Xian Ting; Yang, Huiyong; Zheng, Hui; Zhang, Pengfei; Heterocycles; vol. 96; 3; (2018); p. 509 – 517;,
Nitrile – Wikipedia,
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Application of 3759-28-2, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 3759-28-2 name is 2-(Cyanomethyl)benzonitrile, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

General procedure: A mixture of each of 1 (2.38 g, 0.01 mol) and appropriate nitriles 2a-d (0.01 mol) in the presence ofammonium acetate (1.54 g, 0.02 mol) was heated in an oil-bath at 150 oC for 45 min. The reaction mixturewas poured onto ice/HCl. The solid that separated out was filtered, dried and recrystallized fromEtOH-DMF to give compounds 3a-d.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(Cyanomethyl)benzonitrile, and friends who are interested can also refer to it.

Reference:
Article; Fadda, Ahmed A.; Mohamed, Khaled S.; Refat, Hala M.; El-Bialy, Engy E.; Heterocycles; vol. 91; 1; (2015); p. 134 – 148;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 939-79-7, name is 4-Methyl-3-nitrobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 4-Methyl-3-nitrobenzonitrile

A mixture of 3-nitro-p-tolunitrile (1.2 g; 7.40 mmol), N-bromosuccinimide (2.6 g;14.80 mmol) and benzoyl peroxide (182 mg; 0.75 mmol) in acetic acid (15 mL) in asealed tube was heated at 140C using one single mode microwave (Biotage InitiatorEXP 60) with a power output ranging from 0 to 400 W for 40 mm. The mixture waspoured into ice-water, K2C03 solid and EtOAc were added. The mixture was extracted with EtOAc (3x). The organic layer was dried over MgSO4, filtered and the solvent was evaporated. The residue was taken up with toluene and the solvent was evaporated to give 1.47 g of brown oil of a mixture of intermediate 578 and 3-nitro-p-tolunitrilewhich was used in the next reaction step without any further purification.

According to the analysis of related databases, 939-79-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; STANSFIELD, Ian; QUEROLLE, Olivier Alexis Georges; PONCELET, Virginie Sophie; GROSS, Gerhard Max; JACOBY, Edgar; MEERPOEL, Lieven; KULAGOWSKI, Janusz Jozef; MACLEOD, Calum; MANN, Samuel Edward; GREEN, Simon Richard; HYND, George; (477 pag.)WO2017/125530; (2017); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 23842-82-2, name is 2-Amino-5-methoxybenzonitrile, A new synthetic method of this compound is introduced below., Safety of 2-Amino-5-methoxybenzonitrile

The N-carbethoxy starting material is prepared in the following manner: A mixture of 5-methoxyanthranilonitrile (Bartlett, Dickel and Taylor, J.A.C.S. 80, 136 (1958), 2.25 g) and ethyl chloroformate (60 ml) is heated under reflux for 20 min. and then concentrated to dryness at reduced pressure. The residue is taken up in toluene (20 ml) hexane (50 ml) added and the precipitate collected, washed with hexane and air dried to afford the pure urethane, mp. 142-144.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Ciba-Geigy Corporation; US4713383; (1987); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 52516-37-7, These common heterocyclic compound, 52516-37-7, name is 2-(3,5-Dichlorophenyl)acetonitrile, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

A mixture of 3, 5-dichlorophenylacetonitrile (2gm, prepared according to the procedure described in WO00/58292), ethanol (25mL), potassium hydroxide (3. 95gm) and water (1 OmL) was heated under reflux for 4hr then evaporated to dryness under vacuum. The residue was partitioned between water (20mL) and diethyl ether and the aqueous layer was acidified to pH1 by addition of concentrated hydrochloric acid. The mixture was extracted with diethyl ether (3 x 25mL), the organic layer dried over anhydrous sodium sulfate and evaporated under vacuum. The carboxylic acid was dissolved in methanol (20mL) and TRIMETHYLSILYLDIAZOMETHANE (2M solution in hexanes, 30mL, Aldrich Chemical Company, Milwaukee, WI) was added slowly. After 1 hr the solvent was removed under vacuum, the residue dissolved in diethyl ether, washed with aqueous sodium carbonate solution (2M), dried over anhydrous sodium sulfate and evaporated to dryness to give the title compound (2. 1 GM). 1H-NMR (CDCI3) 6 7. 27 (s, 1H), 7. 17 (s, 2H), 3. 71 (S, 3H), 3. 57 (s, 2H).

The synthetic route of 52516-37-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER PRODUCTS INC.; WO2004/85401; (2004); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Some common heterocyclic compound, 403-54-3, name is 3-Fluorobenzonitrile, molecular formula is C7H4FN, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Computed Properties of C7H4FN

The 4chloro-6-(2-methylimidazol-1-yl)quinazoline used as a starting material was obtained as follows: 3-Fluorobenzonitrile (25 g) was added dropwise to a stirred mixture of potassium nitrate (21.1 g) and concentrated sulphuric acid (150 ml) which had been cooled in a mixture of salt and ice. The mixture was stirred at ambient temperature for 45 minutes. The mixture was poured onto ice (800 ml) and the precipitate was isolated. The solid so obtained was dissolved in methylene chloride, dried (MgSO4) and the solution was evaporated to give 5-fluoro-2-nitrobenzonitrile (19 g).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 403-54-3, its application will become more common.

Reference:
Patent; Zeneca Limited; US5955464; (1999); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts