Premium
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 .