N-[3,3-dimethyl-2-(3-nitro-phenyl)-1,2,3,4-tetrahydro-quinoline-6-carbonyl]-methanesulfonamide → N-[2-(3-Amino-phenyl)-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carbonyl]-methanesulfonamide

Participants

Reaction Conditions

Reaction Steps

To a mixture of N-[3,3-dimethyl-2-(3-nitro-phenyl)-1,2,3,4-tetrahydro-quinoline-6-carbonyl]-methanesulfonamide (2 g, 5 mmol) in ethanol 95% (100 mL) and 10% hydrochloric acid (20 mL) was added iron (0.84 g, 15 mmol). The reaction mixture was stirred at 95° C. for 1 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 N-[2-(3-Amino-phenyl)-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carbonyl]-methanesulfonamide (1.5 g, 80%) as a brown oil which was used for next step without further purification: LC/MS m/e calcd for C19H23N3O3S (M+H)+: 374.48, observed: 374.1.

Provenance & Evidence