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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

A Comparison of the Reactions of Some Ethyl N-Arylcarbamates With Those of the Corresponding Acetanilides. II. Amidomethylation With N-Hydroxy-methylphthalimide

J Rosevear and JFK Wilshire

Australian Journal of Chemistry 43(2) 339 - 353
Published: 1990

Abstract

The reactions of some ethyl N- arylcarbamates and of the corresponding acetanilides towards 1 equiv. of N-hydroxymethylphthalimide in concentrated sulfuric acid at 50° have been compared with one another. In the case of certain para-substituted compounds, amidomethylation occurs more readily ortho to the carbamate group than to the N-acetyl group. The diagnostic use of (D6)benzene as a 1H n.m.r. solvent, particularly for the structural elucidation of the ortho-( phthalimidomethyl )- phenylcarbamates and -acetanilides, is reported. Acidic treatment of the ortho -( phthalimidomethyl ) phenylcarbamates, but not of the corresponding acetanilides, gave 8-substituted isoindolo [1,2-b]quinazolin-12(10H)-ones. Amidomethylation of the parent anilines is also described.

https://doi.org/10.1071/CH9900339

© CSIRO 1990

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