Dichloromethane → O-cyclohexylhydroxylamine hydrochloride

Participants

Reaction Conditions

Reaction Steps

Hydrazine monohydrate (2.24 mL, 42.20 mmol) was added to a solution of 2-cyclohexyloxy-isoindole-1,3-dione (4.88 g, 21.10 mmol) in a mixture of methanol (12 mL) and methylene chloride (120 mL), and the mixture was stirred at 25° C. for 4 h. The resulting precipitate was filtered off in vacuo, and the filtrate was washed with 5.0 N aqueous ammonium hydroxide (60 mL). The aqueous layer was extracted with methylene chloride (2×25 mL). The combined organic layers were washed with brine, dried over magnesium sulfate and concentrated in vacuo. The residue was dissolved in a 4.0 M solution of hydrochloric acid in dioxane (12 mL) and diluted with diethyl ether (70 mL). The resulting precipitate was collected by filtration in vacuo to afford O-cyclohexyl-hydroxylamine hydrochloride (1.71 g, 45.7%) as a white solid, which was used in the next step without further purification.

Provenance & Evidence