HCID 67441792, compound → HCID 67441304, 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-8-carboxylic acid methyl ester (1 g, 2.7 mmol) in ethanol 95% (100 mL) and 10% hydrochloric acid (5 mL) was added iron (0.23 g, 4 mmol). The reaction mixture was stirred at 95° C. for 4 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 2-(3-amino-phenyl)-6-chloro-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-8-carboxylic acid methyl ester (0.8 g, 86%) as a white solid: LC/MS m/e calcd for C19H21ClN2O2 (M+H)+: 345.84, observed: 345.1.

Provenance & Evidence