Medicinal nitro-compounds. Part I. Photo-rearrangement of N-Aryl-2-nitrobenzamides

Brian C Gunn, M F G Stevens

Research output: Contribution to journalArticle

Abstract

2-Nitrobenzanilide (4a) rearranges to 2-(2-hydroxyphenylazo)benzoic acid (5a) on exposure to light. Azoxybenzene-2-carboxylic acid (6a) is an intermediate in this transformation and also rearranges to the acid (5a) in high yield. Other N-aryl-2-nitrobenzamides (4b-f) afford the analogous azo-compounds (5b-f), but when the N-aryl system carries electron-attracting substituants (4g-j) the compounds are photostable. Irradiation of 2-nitro-benzo-m-toluidide (12) yields a mixture of two isomeric azocarboxylic acids. The scope of the rearrangement has been explored: N-(1-naphthyl)-2-nitrobenzenesulphonamide (18) affords the analogous azobenzenesulphonic acid (19) but N-alkyl- or N-aralkyl-2-nitrobenzamides. N-substituted 4-nitrobenzamides, and N,N'-diphenyl-2-nitrobenzamidine (16) do not yield azo- or azoxy-compounds.

Original languageEnglish
Pages (from-to)1682-1688
Number of pages7
JournalJournal of the Chemical Society, Perkin Transactions 1
Publication statusPublished - 1973

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acids
azo compounds
benzoic acid
carboxylic acids
biphenyl
irradiation
electrons
nitro compounds

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title = "Medicinal nitro-compounds. Part I. Photo-rearrangement of N-Aryl-2-nitrobenzamides",
abstract = "2-Nitrobenzanilide (4a) rearranges to 2-(2-hydroxyphenylazo)benzoic acid (5a) on exposure to light. Azoxybenzene-2-carboxylic acid (6a) is an intermediate in this transformation and also rearranges to the acid (5a) in high yield. Other N-aryl-2-nitrobenzamides (4b-f) afford the analogous azo-compounds (5b-f), but when the N-aryl system carries electron-attracting substituants (4g-j) the compounds are photostable. Irradiation of 2-nitro-benzo-m-toluidide (12) yields a mixture of two isomeric azocarboxylic acids. The scope of the rearrangement has been explored: N-(1-naphthyl)-2-nitrobenzenesulphonamide (18) affords the analogous azobenzenesulphonic acid (19) but N-alkyl- or N-aralkyl-2-nitrobenzamides. N-substituted 4-nitrobenzamides, and N,N'-diphenyl-2-nitrobenzamidine (16) do not yield azo- or azoxy-compounds.",
author = "Gunn, {Brian C} and Stevens, {M F G}",
year = "1973",
language = "English",
pages = "1682--1688",
journal = "Journal of the Chemical Society, Perkin Transactions 1",
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Medicinal nitro-compounds. Part I. Photo-rearrangement of N-Aryl-2-nitrobenzamides. / Gunn, Brian C; Stevens, M F G.

In: Journal of the Chemical Society, Perkin Transactions 1, 1973, p. 1682-1688.

Research output: Contribution to journalArticle

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T1 - Medicinal nitro-compounds. Part I. Photo-rearrangement of N-Aryl-2-nitrobenzamides

AU - Gunn, Brian C

AU - Stevens, M F G

PY - 1973

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N2 - 2-Nitrobenzanilide (4a) rearranges to 2-(2-hydroxyphenylazo)benzoic acid (5a) on exposure to light. Azoxybenzene-2-carboxylic acid (6a) is an intermediate in this transformation and also rearranges to the acid (5a) in high yield. Other N-aryl-2-nitrobenzamides (4b-f) afford the analogous azo-compounds (5b-f), but when the N-aryl system carries electron-attracting substituants (4g-j) the compounds are photostable. Irradiation of 2-nitro-benzo-m-toluidide (12) yields a mixture of two isomeric azocarboxylic acids. The scope of the rearrangement has been explored: N-(1-naphthyl)-2-nitrobenzenesulphonamide (18) affords the analogous azobenzenesulphonic acid (19) but N-alkyl- or N-aralkyl-2-nitrobenzamides. N-substituted 4-nitrobenzamides, and N,N'-diphenyl-2-nitrobenzamidine (16) do not yield azo- or azoxy-compounds.

AB - 2-Nitrobenzanilide (4a) rearranges to 2-(2-hydroxyphenylazo)benzoic acid (5a) on exposure to light. Azoxybenzene-2-carboxylic acid (6a) is an intermediate in this transformation and also rearranges to the acid (5a) in high yield. Other N-aryl-2-nitrobenzamides (4b-f) afford the analogous azo-compounds (5b-f), but when the N-aryl system carries electron-attracting substituants (4g-j) the compounds are photostable. Irradiation of 2-nitro-benzo-m-toluidide (12) yields a mixture of two isomeric azocarboxylic acids. The scope of the rearrangement has been explored: N-(1-naphthyl)-2-nitrobenzenesulphonamide (18) affords the analogous azobenzenesulphonic acid (19) but N-alkyl- or N-aralkyl-2-nitrobenzamides. N-substituted 4-nitrobenzamides, and N,N'-diphenyl-2-nitrobenzamidine (16) do not yield azo- or azoxy-compounds.

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