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An improved procedure for the nitration of benzo-2,1,3-selenadiazoles and their reduction to ortho-phenylenediamines

✍ Scribed by S. W. Wright; L. D. Mcclure

Publisher: Journal of Heterocyclic Chemistry
Year: 2004
Tongue: English
Weight: 33 KB
Volume: 41
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.5570410629

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✦ Synopsis

Abstract

A method for the nitration of benzo‐2,1,3‐selenadiazoles using nitric acid dissolved in a mixture of methanesulfonic acid and phosphorus pentoxide at room temperature is presented. The S~N~2Ar displacement of fluoride that is observed when sulfuric acid is used as solvent is prevented and yields are high. Sodium nitrate could be used in place of nitric acid with no loss in yield. Following nitration, the 2,1,3‐selenadiazole ring is cleaved with hydriodic acid to afford a 3‐nitro‐ortho‐phenylenediamine. The method is applied to the multi‐gram preparation of 4‐fluoro‐3‐nitrobenzene‐1,2‐diamine.

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