(E)-2-(5-chloro-2,4-dinitrophenyl)-N,N-dimethylethenamine → 5-Chloro-1H-indol-6-amine

Participants

Reaction Steps

A suspension of (E)-2-(5-chloro-2,4-dinitrophenyl)-N,N-dimethylethenamine (9.8 g, 36 mmol) and Raney Nickel (9.8 g) in EtOH (140 mL) was stirred under H2(1 atm) at room temperature for 4 h. After filtration, the filtrate was concentrated and the residue was purified by column chromatograph (petroleum ether/ethyl acetate=10:1) to give 5-chloro-1H-indol-6-amine (0.97 g, 16%) as a gray powder. 1 HNMR (CDCl3) δ 7.85(br 5, 1 H), 7.52(s, 1 H), 7.03(s, 1H), 6.79(s, 1H), 6.34(s, 1H), 3.91(br s, 1H); MS (ESI) m/e (M+H+) 166.0.

Provenance & Evidence