HCID 67290739, compound → HCID 67290769, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 6-chloro-4,4-dimethyl-2-(2-nitrophenyl)-1,2,3,4-tetrahydroquinoline (7.7 g, 24.3 mmol) in ethanol and 10% hydrochloric acid was added iron powder (7.0 g, 125.4 mmol). The resulting mixture was stirred at 90° C. for 3 h. Then the insoluble solid was filtered off and the filtrate was concentrated in vacuum. The residue was extracted with ethyl acetate, washed with saturated sodium carbonate, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography to give 2-(6-chloro-4,4-dimethyl-1,2,3,4-tetrahydroquinolin-2-yl)aniline (2.5 g, yield 35.7%) LC/MS m/e obsd. (ESI+) [(M+H)+] 287.2.

Provenance & Evidence