反应详情

温度

100 °C

To a stirring solution of 8-fluoro-3,4-dihydroquinolin-2(1H)-one (1.6 g, 9.69 mmol) and acetyl chloride (1.722 mL, 24.22 mmol) in carbon disulfide (20 mL, 9.69 mmol) at 0° C. was added in portions aluminum chloride (6.59 g, 49.4 mmol). The reaction mixture was stirred at 100° C. without a condensor until the solvent evaporated, then a condensor was fitted in place and stirring continued at 100° C. for 4 h. After cooling, the reaction contents were carefully poured into ice water and partitioned between DCM and water. The aqueous layer was extracted with DCM (3×150 mL). The combined organic washes were dried over MgSO4 and concentrated under vacuum to a tan solid. This was purified by flash chromatography on silica gel using 1% MeOH in DCM to give 6-acetyl-8-fluoro-3,4-dihydroquinolin-2(1H)-one as a yellow solid (1.6 g, 80%). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.72 (br. s., 1H), 7.68-7.60 (m, 1H), 2.76-2.58 (m, 2H), 2.58-2.50 (m, 2H), 1.58 (s, 13H). LCMS: R.T.=1.335 min; [M+H]+=208.0.

1. customevaporated
2. customa condensor was fitted in place
3. stirringstirring
4. temperatureAfter cooling
5. customthe reaction contents
6. custompartitioned between DCM and water
7. extractionThe aqueous layer was extracted with DCM (3×150 mL)
8. dry with materialThe combined organic washes were dried over MgSO4
9. concentrationconcentrated under vacuum to a tan solid
10. customThis was purified by flash chromatography on silica gel using 1% MeOH in DCM