反应详情

A mixture of 3-isobutyryl-4-(2-methylphenylamino) 8-hydroxyquinoline (5.0 g, 15.6 mmol), potassium t-butoxide (2.63 g, 23.4 mmol) and 2-chloroethyl methyl ether (2.85 ml, 31.2 mmol) in tetrahydrofuran (250 ml) was heated at reflux for 3 days, then the solvent evaporated. Water was added, the product extracted into dichloromethane, and the organic extracts dried and evaporated. Chromatography (silica gel, ethyl acetate/2% acetic acid/0%-5% methanol) removed unchanged starting material, then further chromatography (silica gel, 1%-1.5% methanol in dichloromethane) and crystallization from petroleum ether (40-60) gave 3-isobutyryl-4-(2-methylphenylamino)-8-(2-methoxyethoxy)quinoline (0.67 g), m.p. 68°-70°.

1. temperaturewas heated
2. temperatureat reflux for 3 days
3. customthe solvent evaporated
4. additionWater was added
5. extractionthe product extracted into dichloromethane
6. customthe organic extracts dried
7. customevaporated
8. customChromatography (silica gel, ethyl acetate/2% acetic acid/0%-5% methanol) removed unchanged
9. customfurther chromatography (silica gel, 1%-1.5% methanol in dichloromethane) and crystallization from petroleum ether (40-60)