Sulfuric Acid → 3-Anilinoprop-2-enenitrile

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Reaction Steps

12.25 g (0.125 mol) of sulfuric acid in 30 ml of ethanol is added drop by drop, at 0° C., to a suspension of 32.5 g (0.25 mol) of sodium-3-hydroxyacrylonitrile and 32.6 g (0.35 mol) of aniline in 150 ml of ethanol, and the mixture is held at 25° C. for 5 h. After removal of the solid by filtration and withdrawal of the solvent, the product is dissolved with water, acidified with dilute sulfuric acid, and extracted with ether. After recrystallization of the concentrated ether extract from carbon tetrachloride, 24.3 g (67.6%) of 3-anilinoacrylonitrile is obtained.

Provenance & Evidence