[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:22]=[CH:21][C:11]2[C:12]3[CH2:13][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:22]=[CH:21][C:11]2[C:12]3[CH2:13][CH2:14][CH2:15][NH:16][C:17]=3[CH2:18][CH2:19][C:10]=2[CH:9]=1147 g (1.94 mol) of lithium aluminum hydride are suspended in 4 l of tetrahydrofuran under argon, 454 g (1.94 mol) of 8-chloro-1,4,5,6-tetrahydrobenzo[f]quinolin-3(2H)-one are slowly added thereto and the mixture is boiled under reflux for 2.5 hours. The mixture is then cooled and 470 ml of 18 percent sodium hydroxide solution are added thereto. The resulting mixture is stirred at room temperature for 30 minutes, filtered and the filter residue is washed with tetrahydrofuran. Upon evaporation of the filtrate, there is obtained 8-chloro-1,2,3,4,5,6-hexahydrobenzo[f]quinoline as a yellow oil.
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