HCID 67290469, compound → HCID 67290159, compound

Participants

Reaction Steps

To a suspension of 4,4-dimethyl-2-(2-nitrophenyl)-1,2,3,4-tetrahydroquinoline-6-carbonitrile (2 g, 6.54 mmol) in saturated aqueous ammonium chloride and ethanol was added iron powder at room temperature. After addition, the resulting mixture was stirred at reflux under nitrogen for 3 h. The reaction mixture was cooled to room temperature and filtered through a pad of celite. The solvent of ethanol in filtrate was removed under reduced pressure and the water phase was extracted with ethyl acetate. The combined organic phase was dried, concentrated to give 2-(2-aminophenyl)-4,4-dimethyl-1,2,3,4-tetrahydroquinoline-6-carbonitrile as white solid (1 g, yield 56%). The product was used for the next step without further purification. LC/MS m/e obsd. (ESI+) [(M+H)+] 228.2.

Provenance & Evidence