Category: 177476-76-5

Synthetic Route of 177476-76-5, These common heterocyclic compound, 177476-76-5, name is 4-Amino-3-methoxybenzonitrile, 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.

N-(4-Cyano-2-methoxyphenyl)formamide Acetic anhydride (0.65 mL, 6.7mmol) was cooled in an ice bath and formic acid (0.38 mL, 10 mmol) was added with stirring. The ice-bath was removed and the mixture was stirred for a further 60 minutes. The reaction was re-cooled in the ice-bath and 4- amino-3-methoxybenzonitrile (0.25 g, 1.58 mmol) was added. The reaction was stirred at ice-bath temperature for 5 minutes, then at room temperature for 60 minutes. The reaction was concentrated in vacuo, azeotroped with toluene and the title compound was precipitated from ether/hexanes as a white powder (255 mg, 71.3%). 1 H NMR (500 MHz, DMSO-d6): delta 10.07 (s, 1 H), 8.39 (s, 1 H), 8.37 (s, 1 H), 7.52 (d, J = 1.7 Hz, 1 H), 7.4 (dd, J = 8.4, 1 .8 Hz, 1 H), 3.92 (s, 3H). LCMS (ESI) R, = 1 .76 minutes MS m/z 177 [M+H]+

The synthetic route of 177476-76-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; HOELDER, Swen; BLAGG, Julian; CHEUNG, Jack; ATRASH, Butrus; SHELDRAKE, Peter; WO2014/37751; (2014); A1;,
Nitrile – Wikipedia,
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Synthetic Route of 177476-76-5, These common heterocyclic compound, 177476-76-5, name is 4-Amino-3-methoxybenzonitrile, 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: Step (A): To a solution of racemic (2?S,3?R,4?S,5?R)-6-chloro-4?-(3-chloro-2-fluoro-phenyl)-2?-(2,2-dimethyl-propyl)-2-oxo-1,2-dihydro-spiro[indole-3,3?-pyrrolidine]-5?-carboxylic acid trifluoroacetic acid salt 17 (R3 = H, R1 = CH2C(CH3)3, Ref. 29) (0.2 g, 0.36 mmol) in dichloromethane (10 mL) was added diisopropylethylamine (0.18 g, 1.4 mmol), diphenylphosphinic chloride (Aldrich) (0.25 g, 1.1 mmol), respectively. The mixture was stirred at room temperature for 0.5 h, then methyl 4-amino-2-methoxybenzoate (Acros) (0.077 g, 0.43 mmol) or methyl 4-amino-3-methoxy-benzoate (Ark Pharm) (0.16 g, 0.9 mmol) was added. The reaction mixture was stirred at room temperature for 20 h. The mixture was concentrated. The residue was partitioned between ethyl acetate and water. The organic layer was separated, washed with water, brine, dried over Na2SO4, then concentrated. The residue was purified by chromatography (3-20% of EtOAc in CH2Cl2) to give a white solid (yield 0.12 g, 54%).

Statistics shows that 4-Amino-3-methoxybenzonitrile is playing an increasingly important role. we look forward to future research findings about 177476-76-5.

Reference:
Article; Zhang, Zhuming; Ding, Qingjie; Liu, Jin-Jun; Zhang, Jing; Jiang, Nan; Chu, Xin-Jie; Bartkovitz, David; Luk, Kin-Chun; Janson, Cheryl; Tovar, Christian; Filipovic, Zoran M.; Higgins, Brian; Glenn, Kelli; Packman, Kathryn; Vassilev, Lyubomir T.; Graves, Bradford; Bioorganic and Medicinal Chemistry; vol. 22; 15; (2014); p. 4001 – 4009;,
Nitrile – Wikipedia,
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Electric Literature of 177476-76-5, These common heterocyclic compound, 177476-76-5, name is 4-Amino-3-methoxybenzonitrile, 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.

4-Amino-3-methoxybenzonitrile (5.93 g, 40 mmol), acetic acid (40 mL) and methanol (100 mL) were added to a 250 mL single neck flask, then bromine (7.03 g, 44 mmol) was added dropwise at 0C. The reaction mixture was stirred for 2 h at rt. To the mixture was added saturated aqueous sodium carbonate (200 mL). The mixture was extracted with ethyl acetate (100 mL x 2). The combined organic phases were washed with saturated brine (100 mL), dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (ethyl acetate/petroleum ether (v/v) = 1/10) to give the title compound as a pale yellow solid (7.63 g, 84%).MS (ES-API, pos. ion) m/z: 227.9 [M + 2]t

Statistics shows that 4-Amino-3-methoxybenzonitrile is playing an increasingly important role. we look forward to future research findings about 177476-76-5.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; YANG, Xinye; HUANG, Changwei; MA, Facheng; ZHANG, Ji; WANG, Xiaojun; ZHANG, Yingjun; (162 pag.)WO2017/36404; (2017); A1;,
Nitrile – Wikipedia,
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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. 177476-76-5, name is 4-Amino-3-methoxybenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 177476-76-5

To a solution of 1 (3.46g, 10mmol) in 2-methoxyethanol (20mL) was charged 4-amino-3-methoxybenzonitrile or 4-amino-3-isopropoxybenzonitrile (11mmol) in 2-methoxyethanol (10mL), and the mixture was then heated to 100C, after which methanesulfonic acid (0.64mL, 0.96g, 11mmol) was added dropwise over 5min below 110C, and then the mixture was heated at 110C for 12h. The slurry was cooled to below 10C. The resulting solids were isolated by filtration and washed with cold 2-methoxyethanol until the filtrate was clear to obtain 2a or 2b. 4.1.1.1 4-((5-chloro-4-((2-(isopropylsulfonyl)phenyl)amino)pyrimidin-2-yl)amino)-3-methoxybenzonitrile (2a) (0025) Yield: 63.2%; MS (ESI) m/z: 458.3 [M+H]+.

According to the analysis of related databases, 177476-76-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Wang, Yu; Chen, Shaowei; Hu, Gang; Wang, Jiao; Gou, Wenfeng; Zuo, Daiying; Gu, Yucheng; Gong, Ping; Zhai, Xin; European Journal of Medicinal Chemistry; vol. 143; (2018); p. 123 – 136;,
Nitrile – Wikipedia,
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