反应详情

12.9 Parts of 2-(4-chloro-2-fluorophenyl)-4,4a,5,6,7,8-hexahydro-3(2H)-cinnolinone was dissolved in 30 parts of glacial acetic acid. To the reaction solution was added a solution of 7.4 parts of bromine in 5 parts glacial acetic acid. After addition was complete, the reaction solution was refluxed for 1.5 hours, then cooled, and the solvent removed under a reduced pressure of 300 mm Hg. The resulting residual brown oil was dissolved in 150 parts of methylene chloride; the organic solution was washed with saturated aqueous sodium bicarbonate solution, dried with anhydrous magnesium sulfate, and the solvent removed under a reduced pressure of 300 mm Hg. The residual brown, oily, solid was chromatographed on alumina, eluting with a mixture of ether (67% by volume) and hexane (33% by volume) to afford 2-(4-chloro-2-fluorophenyl)-5,6,7,8-tetrahydro-3(2H)-cinnolinone as a brown oil that solidified on scratching. Purification was achieved by recrystallization from benzene-hexane to yield 2.5 parts of tan crystalline solid, mp 104°-108°.

1. additionAfter addition
2. temperaturethe reaction solution was refluxed for 1.5 hours
3. temperaturecooled
4. customthe solvent removed under a reduced pressure of 300 mm Hg
5. dissolutionThe resulting residual brown oil was dissolved in 150 parts of methylene chloride
6. washthe organic solution was washed with saturated aqueous sodium bicarbonate solution
7. dry with materialdried with anhydrous magnesium sulfate
8. customthe solvent removed under a reduced pressure of 300 mm Hg
9. customThe residual brown, oily, solid was chromatographed on alumina
10. washeluting with a mixture of ether (67% by volume) and hexane (33% by volume)