HCID 67443108, compound → HCID 67442800, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 3,3-dimethyl-2-(3-nitro-phenyl)-1,2,3,4-tetrahydro-quinoline-6-carbonitrile (4 g, 13 mmol) in ethanol 95% (150 mL) and 10% hydrochloric acid (10 mL) was added iron (2.18 g, 39.2 mmol). The reaction mixture was stirred at 95° C. for 6 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)-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carbonitrile (0.9 g, 25%) as a yellow solid: LC/MS m/e calcd for C18H19N3 (M+H)+: 278.37, observed: 278.1.

Provenance & Evidence