[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([N:9]1[C:21]2[CH:20]=[CH:19][C:18]([C:22](O)=[O:23])=[CH:17][C:16]=2[C:15]2[C:10]1=[CH:11][CH:12]=[C:13]([C:25](O)=[O:26])[CH:14]=2)[CH3:8].[H-].O>C1COCC1.ClCCl.[O-2].[O-2].[Mn+4]>[CH:25]([C:13]1[CH:12]=[CH:11][C:10]2[N:9]([CH2:7][CH3:8])[C:21]3[C:16]([C:15]=2[CH:14]=1)=[CH:17][C:18]([CH:22]=[O:23])=[CH:19][CH:20]=3)=[O:26]LiAlH4 (2.15 g, 56.3 mmol) is added portionwise to a suspension of N-ethylcarbazole-3,6-dicarboxylic acid (5.7 g, 20.12 mmol) in 160 ml of anhydrous THF cooled to 0° C. The suspension is stirred for 1 h 30 min at room temperature and then 1 hour under reflux. After cooling to 0° C., the excess hydride is hydrolyzed with a little water and the salts are filtered off. The filtrate is evaporated to dryness and dried under vacuum to give a yellow solid. The latter is suspended in dichloromethane in the presence of activated manganese dioxide (4 g, 15.16 mmol), and the mixture is stirred overnight at room temperature. 4 g of activated manganese dioxide are added and the mixture is stirred for a further 24 h. The suspension is filtered and the filtrate is evaporated under vacuum to give the expected product.
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