Triethylamine → HCID 67856646, compound

Participants

Reaction Steps

To a suspension of trans-4-amino-5,7-dichloro-2-methoxycarbonyl-1,2,3,4-tetrahydroquinoline hydrochloride (example 9a) (0.200 g, 0.642 mmol) and isonicotinoyl chloride hydrochloride (0.124 g, 0.706 mmol) in anhydrous dichloromethane (20 ml) under an atmosphere of nitrogen was added dry triethylamine (0.307 ml, 2.2 mmol) and the resulting mixture was stirred at room temperature for 1 h. The mixture was then evaporated to dryness in vacuo and the residue was partitioned between water (100 ml) and ethyl acetate (250 ml). The organic layer was separated, washed successively with water (3×100 ml), saturated sodium bicarbonate solution (1×100 ml), brine (1×100 ml), dried (MgSO4) and evaporated. The resulting solid was triturated with ethyl acetate and collected by filtration to give the title compound as colourless crystals (0.200 g) mp 200° C. (dec) δ (DMSO, 360 MHz) 1.82 (1H, ddd, J=13.2, 12.6 and 4.1 Hz, CHACHBHCCHD), 2.27 (1H, dm, J=13.2 Hz, CHACHBHCCHD), 3.72 (3H, s, CO2CH3), 4.07 (1H, dd, J=12.6 and 2.9 Hz, CHACHBHCCHD), 5.27 (1H, m, CHACHBHCCHDNHCO-), 6.70 (1H, d, J=2.0 Hz, 6-H or 8-H), 6.91 (1H, d, J=2.0 Hz, 6-H or 8-H), 6.97 (1H, s, ArNH), 7.77 (2H, dd, J=4.5 and 1.6 Hz, ArH), 8.70 (2H, dd, J=4.5 and 1.6 Hz, ArH), 9.02 (1H, d, J=7.1 Hz, -CHDNHCO-); m/e (CI+) 380 (M+1)+, 123 (100%).

Provenance & Evidence