Sulfuric Acid → N,N-dimethyl-N-[2-(7-hydroxy-1H-indazol-4-yl)ethyl]amine

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Reaction Steps

In an autoclave, 1.2 g of N,N-dimethyl-N-[2-(7-amino-1H-indazol-4-yl)ethyl]amine and 24 ml of 1N sulfuric acid are heated under argon for 16 hours to 180° C. Subsequently the mixture is combined under ice cooling with sodium bicarbonate and extracted by shaking with ethyl acetate/butanol (10:1). The organic phase is dried, concentrated, and the residue is triturated with ethyl acetate, thus obtaining 700 mg of N,N-dimethyl-N-[2-(7-hydroxy-1H-indazol-4-yl)ethyl]amine, mp 233°-234° C., yielding after treatment with methanol and ethereal hydrochloric acid, and recrystallization from methanol/diethyl ether, 680 mg of N,N-dimethyl-N-[2-(7-hydroxy-1H-indazol-4-yl)ethyl]amine, hydrochloride, mp 223°-227° C.

Provenance & Evidence