Hydrocortisone 3,20-bissemicarbazone

Hydrocortisone Crude hydrocortisone bissemicarbazone (50 g) is dissolved at 20° in 2.5 liters of 2.4 N hydrochloric acid under a nitrogen atmosphere. The solution is cooled to 5°, and then a solution of 25 g of sodium nitrite in 250 ml of water is added over a 15 min period, the temperature being maintained at 5 + 1°. The reaction mixture is stirred for an additional 30 min at 5°, then treated with a solution of 150 g of urea in 250 ml of water over a 15 min period and finally neutralized below 15° with 20% sodium hydroxide. The mixture is extracted several times with chloroform and the solvent is evaporated under reduced pressure to give 33 g of crude hydrocortisone, mp 197-203°. Crystallization from acetone-Darco gives 26.4 g (69.5%) of pure hydrocortisone mp 216-221° [oc]d 151° (Diox). 

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