o-Butyl-aniline → N-(2-n-Butylphenyl)-N'-(4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}urea

Participants

Reaction Steps

6,7-Dimethoxy-4-(4-aminophenoxy)quinoline (119 mg) was suspended in toluene (12 ml), after the addition of triethylamine (2.4 ml), triphosgene (133 mg) was added, and the admixture was refluxed with heat for 2 minutes. 2-n-Butylphenylamine (0.13 ml) was added to the reaction mixture, and the admixture was refluxed with heat for 10 minutes. After the addition of aqueous sodium hydrogen carbonate, the reaction mixture was extracted 2 times with chloroform, and the organic layer was then washed with brine and dried with anhydrous sodium sulfate. The solvent was removed by reduced-pressure distillation, and the resulting residue was purified by column chromatography on silica gel eluting with chloroform/acetone (4/1) to obtain 130 mg of the title compound (yield: 69%).

Provenance & Evidence