Ethyl chloroacetate → HCID 85821330, compound

Participants

Reaction Conditions

Reaction Steps

4,4'-Bipyridyl (156 g) was heated with ethyl chloroacetate (245 g) in dry dimethylformamide (400 ml) to 90°- 100° C. After 2 hours a further quantity of ethyl chloroacetate (123 g) was added and the mixture heated a further 2.5 hours at 120° C. The solution was cooled, diluted with chloroform (400 ml), stirred a short time at 0° C., and the solid collected, washed with chloroform and dried. The 1,1'-di-ethoxycarbonylmethyl-4,4'-bipyridylium dichloride so obtained (340 g) was dissolved in concentrated hydrochloric acid and heated under reflux for 3 hours. The mixture was cooled to 0° C., acetone (200 ml) slowly added, and the grey solid collected, washed with acetone, and dried, giving 1,1'-dicarboxymethyl-4,4'-bipyridylium dichloride.

Provenance & Evidence