反应详情

To a solution of 3-isobutyryl-4-(2-methylphenylamino)-8-hydroxyquinoline (5 g, 15.6 mmol) in dry tetrahydrofuran (250 ml) was added potassium t-butoxide (2.63 g, 23.4 mmol), followed by 2-bromoethanol (3.9 g, 31.2 mmol). The stirred mixture was heated under reflux for 16 hours, then a further quantity of potassium t-butoxide (2.63 g, 23.4 mmol) and 2-bromoethanol (3.9 g, 31.2 mmol) added, and heating continued for 2 days. The solvent was evaporated, and the residue treated with aqueous sodium bicarbonate and extracted into dichloromethane. The extracts were dried and evaporated to an oil, which was purified by flash chromatography (silica gel, dichloromethane/methanol) and recrystallization from 40-60 petroleum ether to yield 3-isobutyryl-4-(2-methylphenylamino)-8-(2-hydroxyethoxy)-quinoline (2.25 g), m.p. 154°-156°.

1. temperatureThe stirred mixture was heated
2. temperatureunder reflux for 16 hours
3. temperatureheating
4. customThe solvent was evaporated
5. additionthe residue treated with aqueous sodium bicarbonate
6. extractionextracted into dichloromethane
7. customThe extracts were dried
8. customevaporated to an oil, which
9. customwas purified by flash chromatography (silica gel, dichloromethane/methanol) and recrystallization from 40-60 petroleum ether