Ammonium Chloride → HCID 67290882, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred suspension of ethyl 4,4-dimethyl-2-(2-nitrophenyl)-1,2,3,4-tetrahydroquinoline-6-carboxylate (13.0 g, 36.7 mmol) in ethanol was added iron powder (8.2 g, 146.7 mmol) and saturated aqueous ammonium chloride sat room temperature, the reaction mixture was stirred at 90° C. for 3 h. The insoluble solid was filtered off and filtrated was concentrated in vacuum and the residue was extracted with ethyl acetate, dried over anhydrous sodium sulfate and concentrated in vacuum. The residue was purified by column chromatography to give ethyl 2-(2-aminophenyl)-4,4-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate as yellow solid (5.4 g, yield 45.4%). LC/MS m/e obsd. (ESI+) [(M+H)+] 325.1.

Provenance & Evidence