反应详情

温度

100 °C

To a suspension of 4-(4-methoxypyridin-2-yl)-2-nitrocinnamic acid ethyl ester (659 mg) in acetic acid (11 ml) was added iron powder (673 mg), and the mixture was stirred at 100° C. for 2 hours. After cooling, the reaction mixture was poured into a saturated aqueous sodium hydrogencarbonate solution and filtered, and the filtrate was extracted with dichloromethane-methanol (5:1). The organic layer was washed with brine, dried over sodium sulfate and evaporated under reduced pressure. The residue was dissolved in ethanol (5 ml). To the solution was added a solution of sodium methoxide in methanol (28%, 3 ml), and the mixture was refluxed for 2 hours. After cooling, the reaction mixture was poured into a saturated aqueous ammonium chloride solution and extracted with dichloromethane. The organic layer was washed with brine, dried over sodium sulfate and evaporated under reduced pressure to give 7-(4-methoxypyridin-2-yl)-2-quinolone (140 mg).

1. temperatureAfter cooling
2. filtrationfiltered
3. extractionthe filtrate was extracted with dichloromethane-methanol (5:1)
4. washThe organic layer was washed with brine
5. dry with materialdried over sodium sulfate
6. customevaporated under reduced pressure
7. dissolutionThe residue was dissolved in ethanol (5 ml)
8. additionTo the solution was added a solution of sodium methoxide in methanol (28%, 3 ml)
9. temperaturethe mixture was refluxed for 2 hours
10. temperatureAfter cooling
11. additionthe reaction mixture was poured into a saturated aqueous ammonium chloride solution
12. extractionextracted with dichloromethane
13. washThe organic layer was washed with brine
14. dry with materialdried over sodium sulfate
15. customevaporated under reduced pressure