反应详情

温度

23 °C

A mixture of 5-acetyluracil (0.231 g, 1.5 mmol), 5-quinolinylhydrazine dihydrochloride (0.418 g, 1.8 mmol) and HCl (conc., 0.75 mL, 9 mmol) in n-butanol (15 mL) was heated at reflux for 20 h, cooled to 23° C., and concentrated in vacuo. The residue was dissolved in n-butanol (10 mL). The resulting solution was treated with H2SO4 (conc., 0.96 mL, 18 mmol), heated at reflux for 20 h, cooled to 23° C. and concentrated in vacuo. The residue was partitioned between EtOAc and NaOH (1 M). The aqueous layer was extracted three times with EtOAc. The combined organic extracts were dried over Na2SO4 and concentrated in vacuo. The brown solid residue was purified by flash chromatography (Flash 40S, hexanes-acetone 8:2) to afford 0.279 g (60%) of the desired product as a white solid.

1. temperaturewas heated
2. temperatureat reflux for 20 h
3. concentrationconcentrated in vacuo
4. dissolutionThe residue was dissolved in n-butanol (10 mL)
5. temperatureheated
6. temperatureat reflux for 20 h
7. temperaturecooled to 23° C.
8. concentrationconcentrated in vacuo
9. customThe residue was partitioned between EtOAc and NaOH (1 M)
10. extractionThe aqueous layer was extracted three times with EtOAc
11. dry with materialThe combined organic extracts were dried over Na2SO4
12. concentrationconcentrated in vacuo
13. customThe brown solid residue was purified by flash chromatography (Flash 40S, hexanes-acetone 8:2)