Sodium Hydroxide → HCID 15168492, compound

Participants

Reaction Conditions

Reaction Steps

Trans-2-methoxycarbonyl-4-methoxycarbonylmethyl-5,7-dichloro-1,2,3,4-tetrahydroquinoline (Example 156a) (0.4 g, 0.0012 mol) was dissolved in 50% aqueous methanol (80 ml) with sodium hydroxide (1 g). The reaction mixture was heated at 70° C. for 14 h and the solvents removed under vacuum. The residue was dissolved in water (50 ml), acidified to pH 1 with 1 normal hydrochloric acid and extracted into ethyl acetate (2×50 ml). The combined organic layers were dried (Na2SO4), filtered and concentrated in vacuo to give a residue which was purified by recrystallisation from diethyl ether/hexane to give the title compound as a colourless solid (0.24 g, m.p. 229°-231° C.); δ (250 MHz, DMSO) 1.63 (1H, ddd, J=13.3, 12.4 and 4.0 Hz, CHACHBHCCHD), 2.20 (1H, dm, J=13.3 Hz, CHACHBHCCHD), 2.40 (2H, m, CHEHFCO2H), 3.39 (1H, m, CHACHBHCCHDCHEHFCO2H), 3.98 (1H, dd, J=12.4 and 3.3 Hz, CHACHBHCCHD), 6.57 (1H, br, s, NH), 6.61 (1H, d, J=2.0 Hz, 6-H or 8-H), 6.80 (1H, d, J=2.0 Hz, 6-H or 8-H); m/e (FAB) 304 (M+1); Found C, 47.56; H, 3.70; N, 4.57 C12H11Cl2NO4 requires C, 47.39; H, 3.65; N, 4.61%.

Provenance & Evidence