Hydroxyamine hydrochloride → HCID 13749199, compound

Participants

Reaction Steps

4-Chloro-5-(3-chlorobenzoyl)-1-ethyl-1H-pyrazolo[3,4-b]pyridine (2.65 g) was stirred overnight at 90° in 75 ml of glacial acetic acid containing 3.0 g of hydroxylamine hydrochloride. Sodium acetate (3.5 g) was then added, followed by an additional 1.0 g of hydroxylamine hydrochloride. The reaction mixture was then evaporated and the residue distributed between aqueous sodium bicarbonate and dichloromethane. The organic layer was evaporated and the residue was triturated with methanol and then chromatographed (230-400 mesh silica gel, 10% ethyl acetate/dichloromethane) to give 1.20 g of product, mp 207°-209°. It was combined with the products of several other runs and recrystallized from ethyl acetate to give analytically pure material, mp 209°-210° C.

Provenance & Evidence