Phosphorus oxychloride → 4-Chloro-6-methoxy-7-methyl-quinoline
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[CH3:13])[NH:9][CH:8]=[CH:7][C:6]2=O.P(Cl)(Cl)([Cl:17])=O>>[Cl:17][C:6]1[C:5]2[C:10](=[CH:11][C:12]([CH3:13])=[C:3]([O:2][CH3:1])[CH:4]=2)[N:9]=[CH:8][CH:7]=1Participants
3
Procedure
6-Methoxy-7-methyl-1H-quinolin-4-one (73.9 g) was added to phosphorus oxychloride (160 ml), and the mixture was heated under reflux for 2 hr. The reaction solution was cooled to room temperature, and the solvent was then removed by distillation under the reduced pressure. Chloroform and water were added to the reaction solution, and the aqueous layer was neutralized with an aqueous potassium hydroxide solution. The organic layer was washed with water and saturated brine and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, hexane was added to the residue, and the precipitated crystal was collected by filtration to give 4-chloro-6-methoxy-7-methyl-quinoline (12.7 g, yield 71%).