4-Fluorophenylhydrazine hydrochloride → 6-FLUORO-2,3,4,9-TETRAHYDRO-1H-CARBAZOLE-3-CARBOXYLIC ACID ETHYL ESTER

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Reaction Steps

4-Cyclohexanonecarboxylic acid ethyl ester (77 g, 450 mmol) and 4-fluorophenylhydrazine hydrochloride (72 g, 443 mmol) were refluxed in 1.25 L of anhydrous ethanol overnight. The resulting yellow solution was cooled, crystals filtered, the filtrate evaporated, the residue partitioned between ethyl acetate and water, organic layer dried over sodium sulfate, evaporated, crystallized from ethyl acetate/heptane to give 113 g (98%) of the desired product.

Provenance & Evidence