Ammonia → (1-Tosyl-1H-indol-4-YL)methanamine

Participants

Reaction Steps

A mixture of 1-tosyl-1H-indole-4-carbonitrile (0.5 g, 1.69 mmol), 5% NH3 in methanol (5.0 mL) and Raney Nickel (0.2 g) in methanol (15.0 ml) was hydrogenated at 5 Torr for 6 h at rt. After completion of the reaction, the Raney Nickel was filtered off through a pad of celite under vacuum and washed with methanol (5×2 mL). The combined filtrates were evaporated to dryness under reduced pressure. The residue was washed with 10% diethyl ether in pentane to yield the title compound as a white solid (0.45 g, 78%). [1H-NMR (CDCl3, 300 MHz): δ 7.72-7.59 (m, 3H), 7.44-7.52 (m, 1H), 7.33-6.72 (m, 5H), 4.12-4.01 (m, 2H), 2.27 (s, 3H)].

Provenance & Evidence