Hydrochloric Acid → HCID 15168508, compound

Participants

Reaction Steps

To a suspension of trans-5,7-dichloro-2-methoxy-carbonyl-4-acetylamino-1,2,3,4-tetrahydroquinoline (0.12 g, 0.379 mmol) in methanol (5 ml) was added aqueous lithium hydroxide (0.42 ml of a 1.0M solution, 0.42 mmol) and the resulting mixture was stirred at room temperaure for 7 hours. To this mixture was added additional aqueous lithium hydroxide (0.20 ml of a 1.0M solution, 0.20 mmol) and the mixture was stirred for a further 16 hours. The solution was evaporated to dryness in vacuo and the residue obtained was redissolved in water (50 ml). The solution was acidified to pH 1 with dilute hydrochloric acid and extracted with ethyl acetate (2×30 ml). The combined extracts were washed with brine (30 ml), dried (Na2SO4) and evaporated to give the pure title compound as colourless crystals (0.108 g, 223-225 pc); δ (360 MHz, methanol) 1.70 (1H, ddd, J=13.3, 12.8 and 4.0 Hz, CHACHBHCCHD), 1.95 (3H, s, COCH3), 2.41 (1H, dm, J=13.3 Hz, CHACHBHCCHD), 3.92 (1H, dd, J=12.8 and 3.0 Hz, CHACHBHCCHD), 5.17 (1H, m, CHACHBHCCHD), 6.66 (1H, d, J=2.0 Hz, 6-H or 8-H), 6.72 (1H, d, J=2.0 Hz, 6-H or 8-H); m/e 302 (M+), 198 (100%, m-NHCOCH3, CO2H, H); found: C, 47.65; H, 4.11; N, 9.07. C12H12Cl2N2O3 requires C, 47.55; H, 3.99; N, 9.24%.

Provenance & Evidence