Ammonia → HCID 178422933, compound

Participants

Reaction Steps

6-hydroxy-3-[(1H-imidazol-4-yl)methyl]-2-methylbenzamide hydrochloride. A solution of 6.1 g (23.4 mmoles) of ethyl 6-hydroxy-3-[(1H-imidazol-4-yl)methyl]-2-methylbenzoate (prepared in Example 1.C.4.) in 400 ml of liquid ammonia, is heated in an autoclave at 60° C. for 72 hours. The mixture is then evaporated under reduced pressure and the residue is purified by chromatography on silica gel (eluent: 80:20:0.5 v/v/v ethyl acetate-ethanol-ammonia). 3.3 g of 6-hydroxy-3-[(1H-imidazol-4-yl)methyl]-2-methylbenzamide are obtained. Yield: 61%. The amide, treated in ethanol with 1.1 equivalent of hydrochloric acid, is converted into the hydrochloride. Yield: 66% (after recrystallization from water). M.P.: 262.8° C.

Provenance & Evidence