反应详情

温度

23 °C

To a solution of 3-cyano-5,6,7,8-tetrahydroquinoline 1-oxide (645 mg, 3.7 mmol) was added dropwise under ice cooling trifluoroacetic anhydride (6.22 g, 4.18 ml, 29.6 mmol). The light yellow solution was stirred at 23° C. for 18 h. The mixture was quenched with a solution of sodium hydroxide (1N) and stirred vigorously for 30 minutes, then extracted twice with dichloromethane. The combined organic layers were dried over sodium sulphate, filtered and evaporated. The residue was purified by silica gel flash chromatography with n-heptane/ethyl acetate to give the 8-hydroxy-5,6,7,8-tetrahydroquinoline-3-carbonitrile (562 mg, 87% yield) as a white solid. MS (ISP): m/z=175.1 [M+H]+.

1. customThe mixture was quenched with a solution of sodium hydroxide (1N)
2. stirringstirred vigorously for 30 minutes
3. extractionextracted twice with dichloromethane
4. dry with materialThe combined organic layers were dried over sodium sulphate
5. filtrationfiltered
6. customevaporated
7. customThe residue was purified by silica gel flash chromatography with n-heptane/ethyl acetate