Methyl iodide → 3,8-Dimethoxy quinoline

Reaction equation

[OH:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][C:6]=2[O:12][CH3:13].[OH-].[K+].I[CH3:17]>C(O)C>[CH3:17][O:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][C:6]=2[O:12][CH3:13]

Participants

Procedure

175 mg of 3-hydroxy-8-methoxy quinoline [compound (V)] prepared in example 6 and 66 mg of potassium hydroxide were added to 3 ml of ethanol, and the solution was agitated for 30 minutes. To the solution was added 284 mg of iodomethane, and the solution was agitated for 24 hours. The solvent was removed, and the solution was extracted with dichloromethane. The dichloromethane layer was washed with water and aqueous sodium hydroxide, and dried with anhydrous magnesium sulfate. The dichloromethane was removed by vacuum distillation to give 165 mg of 3,8-dimethoxy quinoline.