Water → HCID 13749202, compound

Participants

Reaction Steps

4-Chloro-1-ethyl-5-(3-methylbenzoyl)-1H-pyrazolo[3,4-b]pyridine (2.0 g) and hydroxylamine hydrochloride (6.0 g) were suspended in 200 ml of acetic acid, and to this was added 0.5 g of p-toluenesulfonic acid monohydrate. The reaction mixture was refluxed for 2 hours and then distributed between water and dichloromethane. The organic phase was washed four times with water and once with saturated sodium bicarbonate solution. It was then evaporated and chromatographed over 230-400 mesh silica gel, eluting with 10% ethyl acetate/dichloromethane. By combining the appropriate fractions, 1.40 g of product was obtained, mp 178°-179°. This product was combined with the product of another run and recrystallized from ethyl acetate to give product of mp 180°-181° C.

Provenance & Evidence