Hydroxyamine hydrochloride → N-{4-[1-(hydroxyamino)ethylidene]cyclohexa-2,5-dien-1-ylidene}methanesulfonamide

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A mixture of 4′-(Methylsulfonylamino)acetophenone (13-5, 5 mmol) and hydroxylamine hydrochloride (0.695 g, 10 mmol) in pyridine (5 mL) was heated at 70° C. for 3 h. The reaction mixture was cooled to room temperature, diluted with H2O, and extracted with EtOAc several times. The combined organic layers were washed with H2O and brine, dried over MgSO4, filtered, and the filtrate was concentrated in vacuo. The residue was purified by flash column chromatography on silica gel using EtOAc:hexanes (1:1) as eluant to 4′-Methylsulfonylamino)acetophenone oxime (13-8, LJO-299).

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