Dimethylacetamide → HCID 178483475, compound

Participants

Reaction Conditions

Reaction Steps

An amount of 8.3 g (50.6 mmol) of (E)-4-(dimethylamino)-2-butenioc acid is added excess of 2.0M oxalyl chloride (10 mL) and refluxed at 60° C. until all the solid is in solution. To a separate flask is added 2.2 g (5.06 mmol) of ′2-(acetylamino)-5-({[(Z)-(6-iodo-1,3-dioxo-2,3-dihydroisoquinolin-4(1H)-ylidene)methyl]amino}methyl)phenyl acetate, and N,N-dimethylacetamide (5 mL) and placed in an ice bath for ten minutes. The mixture containing the acid chloride is cooled to room temperature and evaporated to dryness. Dichloromethane (5 mL) is added and transferred to the flask in the ice bath slowly. The mixture is allowed to stir in the ice bath for 3 hours. It is evaporated and purified by column chromatography with 10% methanol: 80% dichloromethane: 1.5% ammonium hydroxide to give the desired product (1.2 g 43% yield) as a light-brown solid.; mp 185-186° C.

Provenance & Evidence