Cyclopropylamine → 3-Cyclopropylamino-2-(2,3,4,5-tetrafluorobenzoyl)acrylonitrile

Participants

Reaction Steps

A solution of cyclopropylamine (3.3 g) in chloroform (20 ml) is added dropwise to a solution of 3-ethoxy-2-(2,3,4,5-tetrafluorobenzoyl)acrylonitrile (14.0 g) in chloroform (50 ml) with maintaining the internal temperature between 6° C. and 8° C. by using an ice bath. The mixture is allowed to stand overnight at room temperature and then concentrated under vacuum to yield an orange oily residue. The oily residue is dissolved in ethanol and the ethanol is removed in vacuum to afford a crystalline residue. The residue is dissolved in hexane and washed with a 20:1 mixture of hexane and ethanol to yield 3-cyclopropylamino-2-(2,3,4,5-tetrafluorobenzoyl)acrylonitrile (12.6 g) as pale yellow prisms, m.p. 88°-89° C.

Provenance & Evidence