4623-24-9

2-(3-Aminophenyl)acetonitrile is a useful reagent in the synthesis of aminophenylalkylaminopyrrolopyrimidines with antiinfluenza activity.

GENERAL METHOD: To a solution of m-nitrobenzeneacetonitrile (150.1 mg, 0.66 mmol) and ammonium chloride (NH4Cl, 183.6 mg, 3.43 mmol) in a solvent mixture of ethanol/water (EtOH/H2O, 5:1, 6 mL) was added powdered iron (Fe, 184.4 mg, 3.30 mmol) and vigorously stirred for 1 hour at 85 °C. . After completion of the reaction, the mixture was cooled to room temperature and filtered through a diatomaceous earth pad to remove solid impurities. The filtrate was concentrated and the residue was purified by column chromatography (eluent: ethyl acetate/hexane, 20:70) to afford 2-(3-aminophenyl)acetonitrile (10a, 99.2 mg, 76% yield) as a brown oil.

[1] Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 4, p. 577 - 583
[2] Patent: US2015/175557, 2015, A1. Location in patent: Paragraph 0347
[3] Patent: CN107098786, 2017, A. Location in patent: Paragraph 0049-0050
[4] Patent: WO2011/47156, 2011, A1. Location in patent: Page/Page column 82
[5] Patent: WO2009/122180, 2009, A1. Location in patent: Page/Page column 95