Acetyl chloride → Hydrochloric Acid

Participants

Reaction Steps

A solution of hydrogen chloride in methanol was prepared by the cautious addition of acetyl chloride (6 ml) to ice-cooled methanol (25 ml). Trans-2-carboxy-5,7-dichloro-4-(3-aminomethylphenyl)carbonylamino-1,2,3,4-tetrahydroquinoline hydrochloride (87 mg, 0.202 mmol) (Example 81) was dissolved in the HCl/methanol solution and the resulting mixture was stirred in a stoppered flask for 2 h. The methanol and excess hydrogen chloride were removed in vacuo and the product recrystallised from methanol/ether to give the title compound as a colourless crystalline solid (80 mg) m.p. 173° C. (dec). δ (DMSO, 360 MHz) 1.94 (1H, ddd, J=13.7, 13.4 and 3.8 Hz, CHACHBHCCHD), 2.51 (1H, dm J=13.7 Hz, CHACHBHCCHD), 3.81 (3H, s, CH3), 4.10 (1H, dd, J=12.6 and 2.7 Hz, CHACHBHCCHD), 4.23 (2H, s, CH2NH2), 5.36 (1H, m, CHACHBHCCHD), 6.81 (1H, d, J=2.0 Hz, 6-H or 8-H), 6.91 (1H, d, J=2.0 Hz, 6-H or 8-H), 7.56 (1H, t, J=7.7 Hz, Ar-H), 7.65 (1H, d, J=7.8 Hz, Ar-H), 7.77 (2H, m, Ar-H); m/e (FAB+), 408 (M+1), 93 (100%); Found C, 49.05; H, 4.43; N, 8.94; C19H19Cl2N3O3. 1.5HCl requires C, 49.29; H, 4.46; N, 9.08%.

Provenance & Evidence