Triethylamine → 5,6,7,8-Tetrahydro-8-oxo-3-quinolinecarbonitrile

Participants

Reaction Conditions

Reaction Steps

To a solution of 8-hydroxy-5,6,7,8-tetrahydroquinoline-3-carbonitrile (555 mg, 3.19 mmol) in dimethylsuloxide (15 ml) at 23° C. was added triethylamine (1.93 g, 2.66 ml, 19.1 mmol) and sulfur trioxide-pyridin complex (1.52 g, 9.56 mmol). The brown solution was stirred at 23° C. for 2 hours. The reaction mixture was poured on water and extracted twice with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulphate, filtered and evaporated to give of a light brown solid, which was purified by silica gel flash chromatography with dichloromethane/methanol to give the 8-oxo-5,6,7,8-tetrahydroquinoline-3-carbonitrile (286 mg, 52% yield) as a light yellow solid. MS (ISP): m/z=173.1 [M+H]+.

Provenance & Evidence