反应详情

A solution of 6-acetoxy-7-methoxy-1,4-dihydroquinolin-4-one (6.2 g, 28 mmol) and thionyl chloride (75 ml) containing DMF (0.5 ml) was heated at reflux for 1 hour. The volatiles were removed by evaporation. The residue was suspended in methylene chloride (5 ml) and poured slowly into a stirred solution of methanol/ammonium hydroxide. The mixture was partitioned between water and methylene chloride and dried by passing through ,phase separating paper. Removal of the solvent by evaporation gave a solid which was triturated with ether, collected by filtration, washed with ether and dried under vacuum to give 4-chloro-6-hydroxy-7-methoxyquinoline.

1. temperaturewas heated
2. temperatureat reflux for 1 hour
3. customThe volatiles were removed by evaporation
4. additionpoured slowly into a stirred solution of methanol/ammonium hydroxide
5. customThe mixture was partitioned between water and methylene chloride
6. customdried
7. customseparating paper
8. customRemoval of the solvent
9. customby evaporation
10. customgave a solid which
11. customwas triturated with ether
12. filtrationcollected by filtration
13. washwashed with ether
14. customdried under vacuum