Hydrazine hydrate (1:1) → 4-(3,3-Dimethyl-butyryl)-benzylamine

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Reaction Steps

Add hydrazine hydrate (0.189 mL, 3.913 mmol) to a stirred suspension of 2-[4-(3,3-dimethyl-butyryl)-benzyl]-isoindole-1,3-dione (875 mg, 2.609 mmol) in methanol (15 mL). Heat the mixture to reflux overnight. Cool the mixture to room temperature and concentrate in vacuo. Partition the residue between EtOAc and 5N aqueous HCl and wash the acidic aqueous phase again with 5N aqueous HCl. Basify with 5N aqueous NaOH to pH 12. Extract the basic aqueous solution three times with chloroform. Dry the combined organic extracts over Na2SO4, filter and concentrate in vacuo to give the title compound as a yellow oil (411 mg, 77%) that was used without any further purification.

Provenance & Evidence