Nitronium tetrafluoroborate → 6-Bromo-2-methoxycarbonylmethyl-8-nitro-N-ethoxalyltetrahydroquinoline

Participants

Reaction Conditions

Reaction Steps

A solution of 6-bromo-2-methoxycarbonylmethyl-N-ethoxalyltetrahydroquinoline (56.0 g, 0.146 mol) in dichloromethane (500 mL) was added dropwise to a suspension of nitronium tetrafluoroborate (25.0 g, 0.179 mol) in dichloromethane (500 mL) at 0° C. The mixture was stirred for 3 h at 0° C., poured into ice-water 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 3:1 to 2:1 hexane/ethyl acetate to give 52.0 g of the title compound (83%).

Provenance & Evidence