反应详情

温度

90 °C

A mixture of 8-amino-4-chloro-3-ethoxycarbonylquinoline (0.3 g) and ethyl 2-ethoxymethyleneacetoacetate (Annalen, 1897, 297, 16, 0.25 g) was heated at 90° C. for 2.5 hours. The mixture was cooled to ambient temperature and the resulting solid added to diphenyl ether at reflux. The mixture was refluxed for 45 minutes, and cooled to 60° C. The mixture was diluted with carbon tetrachloride (50 ml) and cooled to ambient temperature with stirring. The mixture was filtered and the solid so obtained purified by flash chromatography on silica using increasingly polar mixtures of methanol and chloroform. The product so obtained was recrystallised from methanol to give 3-acetyl-7-chloro-8-ethoxycarbonyl-4-oxo-3,4-dihydro-1,10-phenanthroline in 29% yield, mp 288-290° C.

1. temperatureThe mixture was cooled to ambient temperature
2. temperatureat reflux
3. temperatureThe mixture was refluxed for 45 minutes
4. temperaturecooled to 60° C
5. temperaturecooled to ambient temperature
6. filtrationThe mixture was filtered
7. customthe solid so obtained
8. custompurified by flash chromatography on silica using
9. temperatureincreasingly polar mixtures of methanol and chloroform
10. customThe product so obtained
11. customwas recrystallised from methanol