Hydroxylamine Danazol

Danazol was prepared from 4.32 grams of 17a-ethynyl-2-hydroxymethylene-4-androsten-17p-ol-3-one, 1.00 gram of hydroxylamine hydrochloride, 1.12 grams of fused sodium acetate and 135 ml of acetic acid. To a 500 ml, 3-necked flask, equipped with a sealed Hershberg-type stirrer, a reflux condenser and a stopper, was added the above androstenone derivative in 300 ml of 95% ethanol. Stirring was commenced and a slurry of fused sodium acetate and hydroxylamine hydrochloride in glacial acetic acid was added. 

Fused Heterocycles The /8-dicarbonyl system in the formyl derivative of 17-methyltestosterone shows much the same reactivity as the same array in simpler compounds. Thus, reaction of the formyl derivative 17-1 with hydrazine fuses apyrazolering onto the steroid at positions 2,3 (21-1) (Scheme 5.21). This compound, stanazol, is one of the more frequently abused anabolic agents. Reaction of the same formyl derivative with hydroxylamine goes on to add an isoxazole ring to give danazol (21-2). 

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