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Condensation of N′-methyl-2,6-dimethylphenylhydrazine with cyclohexanone in refluxing benzene gives 8,9-dimethyl-1,2,3,4-tetrahydrocarbazole along with water and ammonia. Yields of the 8,9-dimethyl-1,2,3,4-tetrahydrocarbazole are improved and general decomposition in the reaction mixture minimized if the hydrazine hydrochloride is used. In this case, however, the ammonia is obtained as ammonium chloride contaminated with ~6% of methylammonium chloride. N′-Ethyl-2,6-dimethylphenylhydrazine hydrochloride and N′-methyl-2,6-diethylphenylhydrazine hydrochloride condense with cyclohexanone to give 9-ethyl-8-methyl-1,2,3,4-tetrahydrocarbazole and 8-ethyl-9-methyl-1,2,3,4-tetrahydrocarbazole respectively along with ammonium chloride contaminated with a very small amount of ethylammonium chloride and methylammonium chloride respectively.The results are interpreted in terms of the formation first of the intermediate enamine then the dienone–imine.

Fischer indole synthesis. The reaction of N′-alkyl-2,6-dialkylphenylhydrazines with cyclohexanone