Methyl iodide → HCID 54528366, compound

Participants

Reaction Steps

Eight ml of 1,8-diazabicyclo[5,4,0]-7-undecene was added dropwise to a mixture of 2-amino-1-(ethoxycarbonylmethyl)-3-methylpyridinium bromide (5.5 g; 20 mmol) and dichloromethane (200 ml), and then the mixture was stirred for 30 min at room temperature. To the stirred mixture was dropped 1-cyano-1-(ethoxycarbonyl)-2-ethoxyethylene (3.4 g; 20 mmol) in dichloromethane (100 ml) and the mixture was further stirred for 30 min at room temperature. The mixture was evaporated, and the resultant residue was dissolved in 200 ml of acetone. Methyl iodide (20 ml; 32 mmol) was added to the acetone solution and the solution was heated under reflux for 1.5 hour at 60° C. After standing for several hours at room temperature, the resultant precipitates were removed by filtration. The filtrate was concentrated, and the residue was dissolved in dichloromethane, the solution was washed with water, dried over anhydrous magnesium sulfate, successively. The residue, obtained by evaporating the solvent, was chromatographed over silicagel [eluant: hexane-ethyl acetate (2:1)] to give 3.12 g (yield: 55%) of the titled compound as yellow needles.

Provenance & Evidence