Hydrochloric Acid → 6-bromo-2-methoxycarbonylmethyl-N-ethoxalyltetrahydroquinoline

Participants

Reaction Conditions

Reaction Steps

To a solution of 6-bromo-2-methoxycarbonylmethyltetrahydroquinoline (43.8 g, 0.153 mol) and triethylamine (37.5 g, 0.371 mol) in dichloromethane (700 mL) was added slowly ethyl chlorooxalate (25.5 g, 0.187 mol) at 0° C. The mixture was stirred for 3 h at 0° C., poured into 0.3N hydrochloric acid (750 mL) and extracted with dichloromethane. The organic layer was washed with brine, dried over magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography with 4:1 to 3:1 hexane/ethyl acetate to give 56.9 g of the title compound (97%).

Provenance & Evidence