N-Methylaniline → HCID 22132788, compound

Participants

Reaction Steps

6,7-Dimethoxy-4-(4-aminophenoxy)quinoline (72 mg) was suspended in toluene (7 ml), triphosgene (52 mg) was added, and the admixture was refluxed with heat for 3 hours. N-Methylaniline (0.05 ml) was added to the reaction mixture, and the admixture was refluxed for 1 hour with heat. After the addition of aqueous sodium hydrogen carbonate, the reaction mixture was extracted 2 times with ethyl acetate, 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 (10/1) to obtain 48 mg of the title compound (yield: 46%).

Provenance & Evidence