Synthesis of 1??cyano??2??methylisoindole. A new route to isoindoles

JJ D'Amico, B Stults, PG Ruminski…

Index: D'Amico, John J.; Stults, B. Ray; Ruminski, Peter G.; Wood, Karl V. Journal of Heterocyclic Chemistry, 1983 , vol. 20, p. 1283 - 1286

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Citation Number: 16

Abstract

Abstract The reaction of o-phthaldehyde with potassium cyanide and methylamine hydrochloride afforded 1-cyano-2-methylisoindole (1) in 92% yield. Possible mechanism and supporting nmr, ir, mass spectrum and single X-ray structure analysis for 1 are discussed. The X-ray study revealed that the true structure of 1 can best be represented as a resonance hybrid of the canonical forms a, b, c and d.