Acrylonitrile → 2-Methyl-5-nitrocinnamonitrile

Participants

Reaction Steps

0.2877 g (0.5 millimol) of bis-(dibenzylideneacetone)-palladium(O), 9.98 g (50 millimols) of 2-methyl-5-nitrobenzoyl chloride, 3.31 g (62.5 millimols) of acrylonitrile and 17.68 g (50 millimols) of tris-(2-ethylhexyl)-amine, in 100 ml of cyclopentanone, are stirred for 1.5 hours at 100° C. The crude product is chromatographed on silica gel, in methylene chloride, and is then recrystallised from cyclohexane/carbon tetrachloride. 2.1 g (24% of theory) of 2-methyl-5-nitrocinnamonitrile are obtained in the form of white crystals; melting point 113.2° C.

Provenance & Evidence