2-methoxyethyl benzenesulfonate

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 3-butyryl-4-(2-methylphenylamino)-8-hydroxyquinoline (3.20 g, 10 mmol) and potassium t-butoxide (1.47 g, 12 mmol) in dry tetrahydrofuran (100 ml) was heated at reflux for 5 minutes, then 2-methoxyethyl benzenesulphonate (4.33 g, 20 mmol) added and hearing continued for 18 hours. Evaporation of the solvent, chromatography (silica gel, 1-2% methanol in dichloromethane) and recrystallisation from ethyl acetate gave 3-butyryl-4-(2-methylphenylamino)-8-(2-methoxy-ethoxy)quinoline (1.42 g, 38%), m.p. 75°-77°. at reflux for 5 minutes Evaporation of the solvent, chromatography (silica gel, 1-2% methanol in dichloromethane) and recrystallisation from ethyl acetate