6-nitro-1H-indole-2-carbonitrile → 6-Amino-1H-indole-2-carbonitrile

Participants

Reaction Steps

A mixture of 6-nitro-1H-indole-2-carbonitrile (2.5 g, 13 mmol) and Raney Nickel (500 mg) in EtOH (50 mL) was stirred at room temperature under H2(1 atm) for 1 h. Raney Nickel was removed via filtration and the filtrate was evaporated under reduced pressure to give a residue, which was purified by column chromatography on silica get to give 6-amino-1H-indole-2-carbonitrile (1.0 g, 49%). NMR (DMSO-d6) δ 12.75(br s, 1 H), 7.82(d, J=8 Hz, 1 H), 7.57(s, 1H), 7.42(s, 1 H), 7.15(d, J=8 Hz, 1 H); MS (ESI) m/e (M+H+) 158.2.

Provenance & Evidence