反应详情

A solution of 5-(2-chloro-5-fluorophenyl)cyclohexane-1,3-dione (0.17 g) and ammonium acetate (0.16 g) in ethanol (10 ml) was heated under reflux for 12 hours. The solvent was distilled off under reduced pressure, and the residue was combined with ethyl acetate and then the organic layer was washed successively with aqueous sodium carbonate, water and saturated brine and dried over magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was dissolved in ethanol (3.5 ml) and toluene (6 ml), combined with 3-oxobutylaldehyde dimethyl acetal (0.21 g) and potassium hydroxide powder (34 mg) and then heated under reflux. The mixture was combined with potassium hydroxide powder (7 mg) after 30 minutes and with potassium hydroxide powder (7 mg) and 3-oxobutylaldehyde dimethyl acetal (17 mg) after 1 hour and further with potassium hydroxide powder (7 mg) after 1 hour and 30 minutes, and then stirred at the same temperature for 2 hours. After cooling, the solvent was distilled off under reduced pressure, and then the mixture was extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, and dried over magnesium sulfate. Ethyl acetate was distilled off under reduced pressure, and the residue was subjected to a column chromatography on a silica gel (ethyl acetate-hexane) to obtain 7-(2-chloro-5-fluorophenyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-one.

1. temperatureunder reflux for 12 hours
2. distillationThe solvent was distilled off under reduced pressure
3. washthe organic layer was washed successively with aqueous sodium carbonate, water and saturated brine
4. dry with materialdried over magnesium sulfate
5. distillationThe solvent was distilled off under reduced pressure
6. dissolutionthe residue was dissolved in ethanol (3.5 ml)
7. temperatureheated
8. temperatureunder reflux
9. temperatureAfter cooling
10. distillationthe solvent was distilled off under reduced pressure
11. extractionthe mixture was extracted with ethyl acetate
12. washThe organic layer was washed successively with water and saturated brine
13. dry with materialdried over magnesium sulfate
14. distillationEthyl acetate was distilled off under reduced pressure