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Phthalides and 1,3-indandione. XV. Condensation of phthalic anhydride with acrylacetonitriles

P. Hrnčiar

Komensky University, Bratislava

Abstract: cf. CA 59, 2731a. Condensation of phthalic anhydride with arylacetonitriles at 180-190° gave cyanoarylmethylenephthalides (I) and condensation at 225-235° gave arylmethylenephthalides. The formation of arylmethylenephthalides was explained as follows: from the nitrile, the amide is formed (effect of H₂O liberated by the reaction), which with phthalic anhydride forms the acrylphthalimide, which decomp. to arylacetic acid and phthalimide; then the arylacetic acid is condensed with phthalic anhydride to give arylmethylenephthalides. This was proved by condensation of phthalic anhydride with phenylacetamide. The following I were prepd. (R and m.p. given): Ph, 165-7°; α-naphthyl, 191-3°; and β-naphthyl, 189-91°.

Full paper in Portable Document Format: 179a666.pdf (in Slovak)

Chemical Papers 17 (9) 666–671 (1963)