反应详情

A suspension of 6-bromo-8-fluoro-3,4-dihydroquinoline-2(1H)-thione (157-4, 1.71 g, 6.57 mmol) and acetohydrazide (0.58 g, 7.89 mmol) in n-butanol (7 mL) was refluxed for 18 h under inert atmosphere. After cooling down to ambient temperature, ethyl acetate (10 mL) and water (10 mL) were added. Then the organic phase was separated, and the water phase was extracted with ethyl acetate (5×10 mL). The combined organic phases were washed with brine, dried over Na2SO4, and evaporated under reduced pressure. The crude compound was purified by flash chromatography on silica gel to obtain title compound (white solid). 1H NMR (DMSO-D6, 500 MHz) 6=7.79 (dd, J=2.0 Hz, JHF=11.0 Hz, 1H), 7.63 (s, 1H), 2.95 (br s, 4H), 2.46 (d, JHF=8.5 Hz, 3H).

1. temperaturewas refluxed for 18 h under inert atmosphere
2. customThen the organic phase was separated
3. extractionthe water phase was extracted with ethyl acetate (5×10 mL)
4. washThe combined organic phases were washed with brine
5. dry with materialdried over Na2SO4
6. customevaporated under reduced pressure
7. customThe crude compound was purified by flash chromatography on silica gel