Ethanol → 6-Amino-1-(2-(dimethylamino)ethyl)-8-fluoro-3,4-dihydroquinolin-2(1H)-one

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Reaction Steps

1-(2-(Dimethylamino)ethyl)-8-fluoro-6-nitro-3,4-dihydroquinolin-2(1H)-one (500 mg, 1.77 mmol) was weighed into a round bottom flask equipped with a stirbar. Ethanol (10 mL) and THF (2 mL) were 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 black suspension was stirred for 3 h at room temperature. The solid palladium was then filtered off through a plug of celite and the celite pad washed with methanol. The filtrate was concentrated, then chromatographed on silica gel using 0-10% (2M NH3 in MeOH) in ethyl acetate to give the product. Yield: 325 mg, 72%. EI-MS: 251 (M+, 3), 58 (100).

Provenance & Evidence