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

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

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

Author(s) -

D'Amico John J.,

Stults B. Ray,

Ruminski Peter G.,

Wood Karl V.

Publication year - 1983

Publication title -

journal of heterocyclic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.321

H-Index - 59

eISSN - 1943-5193

pISSN - 0022-152X

DOI - 10.1002/jhet.5570200527

Subject(s) - chemistry , methylamine , yield (engineering) , hydrochloride , potassium , potassium cyanide , mass spectrum , cyanide , stereochemistry , computational chemistry , organic chemistry , ion , materials science , metallurgy

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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