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

Participants

Reaction Steps

A suspension of (E)-2-(5-fluoro-2,4-dinitrophenyl)-N,N-dimethylethenamine (8.0 g, 31 mmol) and Raney Nickel (8 g) in EtOH (80 mL) was stirred under H2(40 psi) at room temperature for 1 h. After filtration, the filtrate was concentrated and the residue was purified by column chromatography (petroleum ether/ethyl acetate=5/1) to give 5-fluoro-1H-indol-6-amine (1.0 g, 16%) as a brown solid. 1 HNMR (DMSO-d6) δ 10.56(br s, 1 H), 7.07(d, J=12 Hz, 1 H), 7.02(m, 1H), 6.71(d, J=8 Hz, 1H), 6.17(s, 1H), 3.91(br s 2H); MS (ESI) m/e (M+H+) 150.1.

Provenance & Evidence