HCID 67441923, compound → HCID 67441715, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 6-chloro-3,3-dimethyl-2-(3-nitro-phenyl)-1,2,3,4-tetrahydro-quinoline (10.5 g, 33 mmol) in ethanol 95% (150 mL) and 10% hydrochloric acid (10 mL) was added iron (3.72 g, 66 mmol). The reaction mixture was stirred at 95° C. for 3 h. Then the insoluble solid was filtered off and the filtrate was concentrated in vacuo and the residue was extracted with ethyl acetate (2×200 mL), washed with 30% sodium hydroxide in water (2×100 mL), dried over anhydrous sodium sulfate and concentrated in vacuo to afford 3-(6-chloro-3,3-dimethyl-1,2,3,4-tetrahydro-quinolin-2-yl)-phenylamine (7.8 g, 82%) as a yellow solid: LC/MS m/e calcd for C17H19ClN2 (M+H)+: 287.81, observed: 287.0.

Provenance & Evidence