Sodium Hydroxide → 8-Chloro-1,1-dimethyl-1,2,3,4,5,6-hexahydrobenzo[f]quinoline

反応式

[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:24]=[CH:23][C:11]2[C:12]3[C:13]([CH3:22])([CH3:21])[CH2:14][C:15](=O)[NH:16][C:17]=3[CH2:18][CH2:19][C:10]=2[CH:9]=1.[OH-].[Na+]>O1CCCC1>[Cl:7][C:8]1[CH:24]=[CH:23][C:11]2[C:12]3[C:13]([CH3:21])([CH3:22])[CH2:14][CH2:15][NH:16][C:17]=3[CH2:18][CH2:19][C:10]=2[CH:9]=1

参加物

実験手順

3.36 g (0.089 mol) of lithium aluminum hydride are suspended in 100 ml of tetrahydrofuran under argon. 11.6 g (0.044 mol) of 8-chloro-1,1 -dimethyl-1,2,5,6-tetrahydrobenzo[f}quinolin-3-one are slowly added thereto and the mixture is boiled under reflux for 2.5 hours. The mixture is then cooled to 0°, 12 ml of 18 percent sodium hydroxide solution are added dropwise thereto and the mixture is filtered. On evaporation of the filtrate, there is obtained 8-chloro-1,1-dimethyl-1,2,3,4,5,6-hexahydrobenzo[f]quinoline as a yellow oil which is processed directly.