Selective reductions of nitroarenes to anilines using metallic zinc in near-critical water

A new procedure for the preparation of anilines (2) in good yield by reduction of the corresponding nitroarenes (1) using Zn in H2O at 220-300 degrees C is described. The procedure is powerful enough to reduce sterically hindered 2-nitro-m-xylene (1c) and is chemoselective for the NO2 groups in 1-ch...

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Bibliographic Details
Published inJournal of the Chemical Society, Perkin Transactions 1 no. 11; pp. 1487 - 1490
Main Authors Boix, C, Poliakoff, N
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 1999
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
HYDROLYSIS
CHEMISTRY
SUPERHEATED WATER
SUPERCRITICAL WATER
ORGANIC-REACTIONS
AQUEOUS-MEDIA
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Summary:A new procedure for the preparation of anilines (2) in good yield by reduction of the corresponding nitroarenes (1) using Zn in H2O at 220-300 degrees C is described. The procedure is powerful enough to reduce sterically hindered 2-nitro-m-xylene (1c) and is chemoselective for the NO2 groups in 1-chloro-2-nitrobenzene (1d) and 1-nitro-3-vinylbenzene (1h). The process involves the reduction of H2O by Zn to generate H-2 followed by hydrogenation of the NO2 group catalysed by residual traces of Zn.
ISSN:0300-922X
1364-5463
DOI:10.1039/a901271k