Hydrochloric Acid → Trans-2-carboxy-5,7-dichloro-4-(3-aminomethylphenyl)carbonylamino-1,2,3,4-tetrahydroquinoline hydrochloride

Participants

Reaction Steps

To a solution of trans-2-carboxy-5,7-dichloro-4-(3-tert-butyloxycarbonylaminomethylphenyl)carbonylamino-1,2,3,4-tetrahydroquinoline (85 mg) in ethyl acetate (20 ml) was added 25 ml of ethyl acetate saturated with hydrogen chloride gas and the mixture was stirred in a stoppered flask for 6 h. The ethyl acetate and excess hydrogen chloride were removed in vacuo and the solid residue was recrystallised from ethyl acetate/methanol to give the title compound as colourless crystals (46 mg), m.p. 199°-200° C. δ (DMSO, 360 MHz) 1.76 (1H, ddd, J=13.2, 13.1 and 3.9 Hz, CHACHBHCCHD), 2.26 (1H, dm J=13.2 Hz, CHACHBHCCHD), 3.96-4.06 (3H, m, ArCH2NH2 and CHACHBHCCHD), 5.29 (1H, m, CHACHBHCCHD), 6.66 (1H, d, J=2.0 Hz, 6-H or 8-H), 6.85 (1H, s, NH), 6.92 (1H, d, J=2.0 Hz, 6-H or 8-H), 7.48 (1H, t, J=7.8 Hz, Ar-H), 7.63 (1H, d, J=7.8 Hz, Ar-H), 7.88 (1H, d, J=7.8 Hz, Ar-H), 8.03 (1H, s, Ar-H), 8.38 (1H, br s, NH2), 8.72 (1H, d, J=7 Hz, NHCO); m/e (FAB+), 394 (M+1), 93 (100%).

Provenance & Evidence