Ethanol → 1-Hydroxy-2-(3,4-dimethoxyphenyl)-4-methyl-5-(3-pyridyl)imidazole

Participants

Reaction Conditions

Reaction Steps

To a suspension of 1-hydroxyimino-1-(3-pyridyl)acetone (1.64 g) in a mixture of dioxane (30 ml), ethanol (10 ml), and water (5 ml) were added 3,4-dimethoxybenzaldehyde (1.66 g) and conc. ammonia water (0.69 ml). The solution was stirred at 60° C. for 2 hours. Additional ammonia water (0.7 ml) was added thereto, and the solution was stirred at 45° to 50° C. for 1 day. The mixture was evaporated, and the residue was dissolved in chloroform, and subjected to column chromatography on silicagel eluting with a mixture of chloroform and methanol. The fractions were collected and evaporated, and the residue was triturated with diisopropyl ether to give 1-hydroxy-2-(3,4-dimethoxyphenyl)-4-methyl-5-(3-pyridyl)imidazole (1.20 g).

Provenance & Evidence