Water → HCID 70546223, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 3-hydroxy-2-(1-imidazolylmethyl)-pyridine (6.0 g) in dry N,N-dimethylformamide (100 ml) was cooled to 5° C. and stirred under nitrogen. Sodium hydride (1.8 g as a dispersion in mineral oil) was added and the mixture was stirred for 1 hour at room temperature and then cooled to 0° C. A solution of 4-cyano-benzylbromide (6.8 g) in dry N,N-dimethylformamide (25 ml) was added and the mixture stirred at room temperature for a further 3 hours and allowed to stand overnight. Water (250 ml) was added and the aqueous solution extracted with ethyl acetate (4×100 ml). The organic extracts were combined, washed with water, dried over MgSO4 and evaporated to yield a solid. Recrystallization from ethyl acetate gave 3-(4-cyanobenzyloxy)-2-(1-imidazolylmethyl)pyridine (12.0 g), m.p. 159° C.

Provenance & Evidence