O-Toluidine → alpha-cyano-beta-(2-methylanilino)-N-ethoxycarbonylacrylamide

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Reaction Steps

Ten grams of α-cyano-β-ethoxy-N-ethoxycarbonylacrylamide in dissolved by heating in 50 ml of ethanol to 60°. Then 5.32 g of 2-methylaniline in 20 ml ethanol is added and the mixture heated at reflux for 4 hours with stirring. Crystals appear on cooling and the mixture is filtered and washed with ether to yield 11.36 g of α-cyano-β-(2-methylanilino)-N-ethoxycarbonylacrylamide, which is dissolved in tetralin and heated at reflux for 3 hours. After cooling, the mixture is filtered, washed with ether, to yield 5-cyano-1-(2-methylphenyl)uracil, m.p. 251.5°-252.5°.

Provenance & Evidence