Norethindrone → Norethisterone-3-oxime

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A solution of norethindrone, 6.5 m moles, and hydroxylamine hydrochloride, 16.4 m moles, in 10 ml of dried pyridine was stirred at room temperature for 48 hours. The progress of the reaction was followed by tlc (thin layer chromatography). The reaction mixture was then heated at 98°C. (bath temperature) for 15 minutes, allowed to cool to 55°C and the pyridine was evaporated in vacuo. The residue was extracted with ether. Drying and removal of the ether gave a residue which was recrystallized from methanol-water and methanol to yield 1.93 g (95%) of norethindrone oxime, mp 121.5°-123°C. Tlc with ethyl acetate: petroleum ether; acetone 1:1:0.2 indicated the product to be a mixture of the syn and anti isomers of the oxime.

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