2-(8-Fluoro-6-nitro-3,4-dihydroquinolin-1(2H)-yl)-N,N-dimethylethanamine → 1-(2-(Dimethylamino)ethyl)-8-fluoro-1,2,3,4-tetrahydroquinolin-6-amine

Participants

Reaction Steps

2-(8-Fluoro-6-nitro-3,4-dihydroquinolin-1(2H)-yl)-N,N-dimethylethanamine (340 mg, 1.27 mmol) was weighed into a round bottom flask equipped with a stir bar. Ethanol (8 mL) was added, followed by Pd (10 wt. % on activated carbon). The flask was fitted with a balloon of hydrogen, evacuated of air and backfilled with hydrogen. The reaction mixture was stirred for 2 h at room temperature under balloon pressure. The reaction mixture was then filtered through a pad of celite and the pad washed with methanol. The filtrate was concentrated, then chromatographed on silica gel using 0-10% (2M NH3 in MeOH) in dichloromethane. Yield: 270 mg, 89%. ESI-MS: 238 (MH+, 100), 193 (37), 147 (31).

Provenance & Evidence