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

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Reaction Steps

A mixture of 6-nitro-1H-indole-2-carbonitrile and 4-nitro-1H-indole-2-carbonitrile (2.5 g, 13.4 mmol) and Raney Ni (500 mg) in EtOH (50 mL) was stirred at room temperature under H2 (1 atm) for 1 h. Raney Ni was filtered off. The filtrate was evaporated under reduced pressure and purified by column chromatography to give 6-amino-1H-indole-2-carbonitrile (B-5) (1 g, 49%). 1H NMR (DMSO-d6) δ 12.75 (br s, 1 H), 7.82 (d, J=8 Hz, 1 H), 7.57 (s, 1 H), 7.42 (s, 1 H), 7.15 (d, J=8 Hz, 1 H); ESI-MS 158.2 m/z (MH+).

Provenance & Evidence