Tag: M.W=100-200

Electric Literature of 1591-37-3, 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. 1591-37-3 name is 2-Amino-6-methoxybenzonitrile, 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.

EXAMPLE 36 2′-Cyano-3′-methoxyoxanilic acid ethyl ester. 80/71 2-Amino-6-methoxybenzonitrile (4.67 g, 0.0315 mole) is condensed with 3.88 ml (0.0346 mole) of ethyl oxalylchloride in a manner similar to example 3, giving 5.0 g of the title compound, m.p. 142-145C., after crystallization from toluene. Elemental Analysis for C12 H12 N2 O4: Calc’d: C, 58.06; H, 4.87; N, 11.29. Found: C, 58.21; H, 4.93; N, 11.02.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Amino-6-methoxybenzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; American Home Products Corporation; US3966965; (1976); A;,
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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. 90401-84-6, name is 6-Cyano-1-tetralone, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C11H9NO

Step 3: 6-Bromo-5-oxo-5,6,7,8-tetrahydronaphthalene-2-carbonitrile Bromine (0.8 mL, 15.7 mmol) was added to a solution of 5-oxo-5,6,7,8-tetrahydro-naphthalene-2-carbonitrile (2.7 g, 15.7 mmol), prepared in the previous step, in dry methylene chloride (55 mL) at 0 C. The reaction was warmed to room temperature. After 2 h, the reaction was diluted with methylene chloride and washed with 5% sodium thiosulfate and brine. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give 4.3 g of crude product. Purification of the crude product on silica gel using 10% ethyl acetate:hexane as the eluent gave 6-bromo-5-oxo-5,6,7,8-tetrahydronaphthalene-2-carbonitrile (3.2 g, 81%), MS(ES) m/z 251 [M+H]+.

According to the analysis of related databases, 90401-84-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Wyeth; US2008/45578; (2008); A1;,
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Related Products of 53312-79-1, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 53312-79-1, name is 3-Amino-4-chlorobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

j00316j A mixture of 3-amino-4-chlorobenzonitrile (1.0 g, 6.6 mmol) and potassium 0-ethyl carbonodithioate (2.1 g, 13.1 mmol) in 1-methylpyrrolidin-2-one (5 mL) at 25 C was degassed and purged with nitrogen 3 times. The mixture was stirred at 120 C for 10 hours, then poured into ice water (200 mL) and acidified with 1 mL concentrated hydrochloric acid, resulting in formation of a solid. The solid was collected by filtration, washed with water (3 x 10 mL) and dried in vacuo to give compound B-22 (1.1 g, crude) as a yellow solid, which was used directly without further purification. LCMS (B): tR=0.613 mi, (ES) mz (M+H) = 193.1.

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, 3-Amino-4-chlorobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; FORUM PHARMACEUTICALS, INC.; ACHARYA, Raksha; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; COOK, Andrew, Simon; HARRISON, Bryce, Alden; McRINER, Andrew, J.; (267 pag.)WO2017/69980; (2017); A1;,
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Synthetic Route of 3544-25-0, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 3544-25-0, name is 2-(4-Aminophenyl)acetonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

1. 4-Hydrazinobenzylcyanide. Hydrochloride A solution of NaNO2 (80 g, 1.16 mol) was added dropwise to a cooled (-10 C.), stirred, suspension of 4-aminobenzyl cyanide (153.5 g, 1.16 mol) in concentrated HCl (1500 ml), at such a rate that the temperature did not rise above -10 C. The mixture was stirred at -10 C. for 0.25 h before being filtered rapidly under vacuum into an addition funnel. The solution was added portionwise over a 0.25 h period to a rapidly stirred mixture of SnCl2.2H2 O (1.05 kg, 4.64 mol) in concentrated HCl (800 ml) keeping the temperature below -5 C. The mixture was allowed to warm to room temperature and stir for 0.25 h before filtering the sandy coloured precipitate under vacuum and washing with ether (5*500 ml). The resultant solid was dried over P2 O5 in a vacuum oven (80 C.) for 16 h to give the title compound (213 g, 100%), m.p. 181-183 C.; 1 H NMR (360 MHz, D2 O) delta 3.90 (2H, s, CH2); 7.06 (2H, d, J=8.7 Hz, Ar-H); 7.40 (2H, d, J=8.7 Hz, Ar-H).

The synthetic route of 2-(4-Aminophenyl)acetonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck Sharp & Dohme Limited; US5298520; (1994); A;,
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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. 127946-77-4, name is 1-Amino-1-cyclopropanecarbonitrile hydrochloride, A new synthetic method of this compound is introduced below., Quality Control of 1-Amino-1-cyclopropanecarbonitrile hydrochloride

A solution of 2-[3-({3-(4-chlorophenyl)-5-oxo-4-[(2S)-3,3,3-trifluoro-2-hydroxypropyl]-4,5- dihydro- 1 H- 1 ,2,4-triazol- 1 -yl } methyl)- IH- 1 ,2,4-triazol- 1 -yl]pyridine-3-carboxylic acid (Example 33A, 80.0 mg, 157 muiotaetaomicron) in N,N-dimethylformamide (1.0 ml) was treated with HATU (89.5 mg, 235 muiotaetaomicron) and stirred 30 min at room temperature. 1-Aminocyclopropanecarbonitrile hydrochloride (1: 1) (27.9 mg, 235 muiotaetaomicron) was then added followed by and N,N- diisopropylethylamine (120 mu, 710 mumol). The resulting mixture was stirred 2 h at room temperature. Purification by preparative HPLC (Method 4) afforded 72.0 mg (80 % of th.) of the title compound. LC-MS (Method 2): Rt = 1.60 min; MS (ESIpos): m/z = 574.1 [M+H]+ -NMR (400 MHz, DMSO-d6) delta [ppm] : 9.23 (d, 2H), 8.64 (dd, IH), 8.08 (dd, IH), 7.83-7.53 (m, 5H), 6.92 (d, IH), 5.08 (s, 2H), 4.41-4.21 (m, IH), 4.08-3.75 (m, 2H), 1.60-1.11 (m, 4H).

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; BAYER AKTIENGESELLSCHAFT; BAYER PHARMA AKTIENGESELLSCHAFT; COLLIN-KROePELIN, Marie-Pierre; KOLKHOF, Peter; NEUBAUER, Thomas; FUeRSTNER, Chantal; POOK, Elisabeth; WITTWER, Matthias, Beat; LUSTIG, Klemens; TINEL, Hanna; LINDNER, Niels; SCHIRMER, Heiko; (449 pag.)WO2019/81307; (2019); A1;,
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Electric Literature of 14618-78-1, A common heterocyclic compound, 14618-78-1, name is 4,4-Dimethoxybutanenitrile, molecular formula is C6H11NO2, 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.

Reference Example 68 2-formyl-4,4-dimethoxybutanenitrile Lithium diisopropylamide mono(tetrahydrofuran) (1.5 M in cyclohexane, 22.0 mL, 33.00 mmol) was added to THF (100 mL) at -30 C. and the resulting solution was stirred for 10 min before 3-cyanopropionaldehyde dimethyl acetal (3.90 mL, 29.90 mmol) was added dropwise over 5 min. After 15 min, methyl formate (2.80 mmol, 45.42 mmol) was added and the resulting solution was stirred at -20 C. to -15 C. for 2 h. The reaction mixture was quenched with water (100 mL) and washed with ether (2*50 mL, discarded). The aqueous layer was acidified with 10% HCl and extracted with ether (3*50 mL). The combined ether extracts were washed with brine (3*50 mL), dried (MgSO4), and concentrated. The residue was dissolved in dichloromethane and concentrated to remove traces of THF and provide 2.28 g (49%) of the title compound as a pale yellow oil.

The synthetic route of 14618-78-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ortho-McNeil Pharmaceutical, Inc.; US6613747; (2003); B2;; ; Patent; Henninger, Todd C.; Xu, Xiaodong; US2002/115620; (2002); A1;,
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Synthetic Route of 873-32-5, A common heterocyclic compound, 873-32-5, name is 2-Chlorobenzonitrile, molecular formula is C7H4ClN, 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.

General procedure: A 50-mL Schlenk tube was charged with aryl halide (1.63 mmol), aryl boronic acid (2.61 mmol), KOH (3.26 mmol), complex 17d (0.5 mol %), TBAB (0.5 mol % relative to the aryl halide) and water (2 mL). The sealed mixture was stirred at 120 C until TLC analysis confirmed completion of the reaction (for GC analysis the products were extracted with toluene). The aqueous solution was then extracted with ethyl acetate (3 10 mL). The combined organic phases were dried over MgSO4, filtered and evaporated in vacuo. The residue product was purified by column chromatography on silica gel using a mixture of hexane and ethyl acetate as eluent to yield biaryls 23a-m:

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:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 3544-25-0, name is 2-(4-Aminophenyl)acetonitrile, belongs to nitriles-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 3544-25-0, Computed Properties of C8H8N2

General procedure: Propionyl chloride (6.0mmol) in dry CH2Cl2 (10mL) was added dropwise to a mixture of 4-methoxybenzenamine (5.0mmol), sodium bicarbonate (12.5mmol) and dry CH2Cl2 (15mL). The mixture was stirred in ice water bath for 1h and poured into water and then extracted with CH2Cl2 (3¡Á30mL). The combined organic layer was washed with brine and dried over anhydrous MgSO4. The solvent was evaporated to dryness to afford the compound 4a. Others amide derivatives 4b-4s were synthesized similarly. Physical constants and spectral data of compounds 4a-4s are summarized below.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(4-Aminophenyl)acetonitrile, and friends who are interested can also refer to it.

Reference:
Article; Ji, Qinggang; Yang, Dan; Wang, Xin; Chen, Chunyan; Deng, Qiao; Ge, Zhiqiang; Yuan, Lvjiang; Yang, Xiaolan; Liao, Fei; Bioorganic and Medicinal Chemistry; vol. 22; 13; (2014); p. 3405 – 3413;,
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Application of 51762-67-5, A common heterocyclic compound, 51762-67-5, name is 3-Nitrophthalonitrile, molecular formula is C8H3N3O2, 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.

The synthetic procedure was adopted from Mayukh etal. with some modifications [37]. A mixture of 4-mercaptophenol (1.26g, 0.01mol) and K2CO3 (4.15g, 0.03mol) in dry dimethylformamide (DMF) (25mL) was stirred vigorously in nitrogen atmosphere for 30min and then 3-nitrophthalonitrile (1.75g, 0.01mol) was added into the reaction mixture followed by a stirring for 16h at 90C. The reaction mixture was allowed to cool room temperature and poured into 1M HCl and the precipitate formed was filtered off and washed with water until the filtrate was neutral and dried in vacuum. The precipitate was extracted with ethyl acetate. The combined organic phases were treated with distilled water, dried with anhydrous sodium sulfate and solvent removed under reduced pressure to obtain solid orange colored powder. The product was further purified by chromatography over a silica gel column using Ethyl acetate and hexane (3:1) mixture as eluent. Yield: 1.73g, (68%); m.p. 162-164C. FT-IR numax/cm-1; 3403 (Ar-OH), 3077-2923 (Ar-H), 2241 (C?N). 1H NMR (DMSO-d6) delta/ppm: 10.18 (s, 1H, Ar-OH), 7.84 (d, 1H, Ar-H), 7.68 (t, 1H Ar-H), 7.42 (d, 2H, Ar-H), 7.09 (d, 1H, Ar-H), 6.91ppm (d, 2H, Ar-H); 13C NMR (DMSO-d6) delta/ppm: 160.21 (aromatic C-O), 147.51, 137.76, 134.51, 130.96, 117.97, 116.40 (C?N), 114.57, 110.27. Anal. Calcd. for C14H8N2OS (252.291g/mol); C 66.65, H 3.20, N 11.10; Found: C 66.56, H 3.09, N 11.08. MS (GC/MS): m/z: 252 [M]+.

The synthetic route of 51762-67-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Suerguen, Serdar; Arslano?lu, Yasin; Hamuryudan, Esin; Dyes and Pigments; vol. 100; 1; (2014); p. 32 – 40;,
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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. 89001-53-6, name is 2-Methyl-4-nitrobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 2-Methyl-4-nitrobenzonitrile

Intermediate IA: (?)-2-(2-(Dimethylammo)vinyl)-4-nitrobenzonitrile; [00186] A mixture of 2-methyl-4-nitrobenzonitrile (5.0 g, 31 mmol) and tert- butoxybis(dimethylamino)methane (12.2 mL, 59 mmol) in dry DMF (8 mL) was stirred at 70 C for 2 h under N2. After cooling to it, DMF was removed in vacuo and the crude product was triturated with hexanes/EtOAc (5:1). The solid was collected by filtration and washed with hexane to give Intermediate IA (6.5 g, 97%) as black solid. 1HNMR (400 MHz, CDCl3) delta 2.97 (s, 6H), 5.36 (d, J = 13.2 Hz, IH), 7.16 (d, J= 13.6 Hz, IH), 7.52 (d, J= 8.8 Hz, IH), 7.60 (m, IH), 8.11 (d, J= 1.8 Hz, IH).

According to the analysis of related databases, 89001-53-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2007/76431; (2007); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts