8-Hydroxyquinoline → 5-Acetyl-8-hydroxyquinoline hydrochloride

反応式

[OH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.[C:12]([Cl:15])(=[O:14])[CH3:13].[Cl-].[Al+3].[Cl-].[Cl-]>C(Cl)CCl>[ClH:15].[C:12]([C:5]1[CH:4]=[CH:3][C:2]([OH:1])=[C:11]2[C:6]=1[CH:7]=[CH:8][CH:9]=[N:10]2)(=[O:14])[CH3:13]

参加物

反応条件

温度: 70 °C

実験手順

8-hydroxyquinoline (500 gms/3.44 moles) was dissolved in ethylene chloride (5 lits) at 25-30° C. in an inert atmosphere. To this solution was added acetyl chloride (260 ml/4.12 moles) drop wise in 2 hours. The reaction mass was stirred for 15-20 minutes. Then, aluminum chloride (1.15 Kg/8.62 moles) was added in lots in 2 hours. The reaction mass was stirred at 25-30° C. for 15-20 minutes and heated to 70° C. for 13-14 hours. After completion of reaction, the reaction mass was cooled to 25-30° C. and slowly quenched in a mixture of crushed ice (10 Kg) and conc. HCl (500 ml). The resulting slurry was stirred for 15-20 minutes. The crude 5-acetyl-8-hydroxyquinoline hydrochloride was isolated by filtration, washed with 2 liters of acetone and dried under vacuum for 1 hour. Yield: 680 gms.