反应详情

温度

23 °C

To a solution of 8-hydroxy-5,6,7,8-tetrahydroquinoline-3-carbonitrile (555 mg, 3.19 mmol) in DMSO (15 ml) at 23° C. was added triethylamine (1.93 g, 2.66 ml, 19.1 mmol) and sulphur trioxide-pyridine 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 Na2SO4, 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, 1.66 mmol, 52.1% yield) as a light yellow solid. MS (ISP): m/z=173.1 [(M+H)+].

1. additionThe reaction mixture was poured on water
2. extractionextracted twice with ethyl acetate
3. washThe combined organic layers were washed with brine
4. dry with materialdried over Na2SO4
5. filtrationfiltered
6. customevaporated
7. customto give of a light brown solid, which
8. customwas purified by silica gel flash chromatography with dichloromethane/methanol