Synthesis
General procedure for the synthesis of 2-(4-aminophenyl)-2-methylpropionitrile from 2-methyl-2-(4-nitrophenyl)propanenitrile: 2-methyl-2-(4-nitrophenyl)propanenitrile (1.0 mmol) was dissolved in ethyl acetate (20 mL) and stannous chloride dihydrate (3.52 g, 15.86 mmol) was added. The reaction mixture was stirred at room temperature overnight. Upon completion of the reaction, the reaction mixture was alkalized with aqueous sodium carbonate. The organic layer was separated, washed with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the crude product. The crude product was purified by silica gel column chromatography with the eluent of ethyl acetate/petroleum ether (1:9, v/v) to afford 2-(4-aminophenyl)-2-methylpropanenitrile (0.45 g, 89% yield) as an oil.
References
[1] Journal of Medicinal Chemistry, 2014, vol. 57, # 11, p. 4834 - 4848
[2] Patent: US2009/137595, 2009, A1
[3] Patent: WO2012/116237, 2012, A2. Location in patent: Page/Page column 119
[4] Patent: US2015/320727, 2015, A1. Location in patent: Paragraph 0555; 0556
[5] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 24, p. 7585 - 7596
