反应详情

A mixture of 8-(2,6-dichlorobenzoylamino)-3-methylquinoline (108 mg), N-bromosuccinimide (69.6 mg) and 2,2'-azobis(2,4-dimethyl-4-methoxyvaleronitrile) (10.1 mg) in dichloromethane and carbon tetrachloride was refluxed for 2 hours. After cooling, the mixture was diluted with ethyl acetate, washed with water, saturated sodium bicarbonate solution and brine, dried over magnesium sulfate and evaporated in vacuo to give a residue containing 3-bromomethyl-8-(2,6-dichlorobenzoylamino)quinoline. The residue was dissolved in dimethylformamide, and acetic acid (27.5 mg) and potassium carbonate (63.2 mg) were added thereto. After stirring for 3 hours at ambient temperature, the mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel (ethyl acetate-dichloromethane) to give 3-acetoxymethyl-8-(2,6-dichlorobenzoylamino)quinoline (48.4 mg).

1. temperaturewas refluxed for 2 hours
2. temperatureAfter cooling
3. washwashed with water, saturated sodium bicarbonate solution and brine
4. dry with materialdried over magnesium sulfate
5. customevaporated in vacuo
6. customto give a residue
7. extractionextracted with ethyl acetate
8. washThe organic layer was washed with brine
9. dry with materialdried over magnesium sulfate
10. customevaporated in vacuo
11. customThe residue was purified by column chromatography on silica gel (ethyl acetate-dichloromethane)