Ammonium Chloride → 5-Chloro-3-cyclohexyl-1,3-dihydro-3-hydroxyindol-2-one

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Reaction Steps

A suspension of 18.15 g of 5-chloroisatin in 45 ml of THF is cooled to +4° C., 200 ml of a 2M solution of cyclohexylmagnesium chloride in ether are added dropwise and the mixture is stirred for 3 hours at RT. 900 ml of a saturated solution of ammonium chloride are added and the solvents are concentrated under vacuum. The aqueous phase is extracted with AcOEt, the organic phase is washed with a saturated solution of NaCl and dried over sodium sulfate and the solvent is evaporated off under vacuum to give 4 g of the expected product after crystallization from a THF/AcOEt mixture.

Provenance & Evidence