2-Chloroethyl methyl ether → HCID 10340699, compound

Participants

Reaction Steps

A solution of 3-butyryl-4-(4-fluoro-2-methylphenylamino)-8-hydroxyquinoline (3.38 g, 10 mmol) and potassium t-butoxide (1.68 g, 15 mmol) in tetrahydrofuran (75 ml) was warmed to near boiling, chloroethyl methyl ether (1.83 ml, 20 mmol) added, and the mixture heated at reflux for 3 days. The solvent was evaporated then the product taken up in dichloromethane, washed with water and brine, dried and evaporated. Chromatography (silica gel, ethyl acetate/2% acetic acid/0%-5% methanol) and recrystallization from ethyl acetate/petroleum ether gave 3-butyryl-4-(4-fluoro-2-methylphenylamino)-8-(2-methoxyethoxy)quinoline (0.41 g), m.p. 124°-5°.

Provenance & Evidence