Electric Literature of 7251-09-4, 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. 7251-09-4, name is 4-Amino-2-methoxybenzonitrile, This compound has unique chemical properties. The synthetic route is as follows.
A suspension of 6-chloro-7-hydroxy-2-oxo-l,2-dihydroquinoline-3- carbaldehyde (58.0 mg, 0.259 mmol) and 4-amino-2-methoxybenzonitrile (48.0 mg, 0.324 mmol) in DCM (4.0 mL) was treated with acetic acid (0.07 mL, 1.223 mmol) and stirred 10 minutes. Sodium triacetoxyborohydride (84.0 mg, 0.396 mmol) was added. The mixture was stirred at room temperature overnight. The mixture was diluted with EtOAc (50 mL), washed with water (2×50 mL) and brine (50 mL), dried (Na2S04), filtered, and evaporated under reduced pressure. The residue was dissolved in methanol, treated with silica gel, and evaporated. The material was chromatographed by Biotage MPLC (10 g silica gel column) with 20 to 100% EtOAc in hexanes to provide the title compound 1-57 (18.6 mg, 0.052 mmol, 20.2 % yield) as a peach-coloured solid. 1H NMR (300 MHz, DMSO-d6): delta ppm 11.82 (s, 1 H), 10.89 (s, 1 H), 7.70 (s, 1 H), 7.63 (s, 1 H), 7.28 (d, J=8.50 Hz, 1 H), 7.12 (dd, J=6.00, 6.00 Hz, 1 H), 6.91 (s, 1 H), 6.32 (d, J=1.76 Hz, 1 H), 6.22 (dd, J=8.60, 1.60 Hz, 1 H), 4.17 (d, J=5.60 Hz, 2 H), 3.78 (s, 3 H). LCMS (Method 4): Rt 1.17 min., m/z 356.1 [M+H]+.
The chemical industry reduces the impact on the environment during synthesis 4-Amino-2-methoxybenzonitrile. I believe this compound will play a more active role in future production and life.
Reference:
Patent; FORMA THERAPEUTICS, INC.; ASHWELL, Susan; CAMPBELL, Ann-Marie; CARAVELLA, Justin Andrew; DIEBOLD, R. Bruce; ERICSSON, Anna; GUSTAFSON, Gary; LANCIA, David R.; LIN, Jian; LU, Wei; WANG, Zhongguo; (141 pag.)WO2016/44782; (2016); A1;,
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