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

John J. D'Amico; B. Ray Stults; Peter G. Ruminski; Karl V. Wood

doi:10.1002/jhet.5570200527

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

John J. D'Amico, B. Ray Stults, Peter G. Ruminski, Karl V. Wood

Section of Stem Cell Biology

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22 Scopus citations

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.

Original language	English
Pages (from-to)	1283-1286
Number of pages	4
Journal	Journal of Heterocyclic Chemistry
Volume	20
Issue number	5
DOIs	https://doi.org/10.1002/jhet.5570200527
State	Published - Jan 1 1983

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title = "Synthesis of 1‐cyano‐2‐methylisoindole. A new route to isoindoles",

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.",

author = "D'Amico, {John J.} and Stults, {B. Ray} and Ruminski, {Peter G.} and Wood, {Karl V.}",

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AU - Stults, B. Ray

AU - Ruminski, Peter G.

AU - Wood, Karl V.

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N2 - 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.

AB - 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.

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DO - 10.1002/jhet.5570200527

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

Abstract

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