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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 38, 2008 - Issue 16
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Original Articles

Preparation of Nitroanilines by Ammonolysis of Multinitrobenzenes

, &
Pages 2782-2786 | Received 24 Oct 2007, Published online: 25 Aug 2010
 

Abstract

Highly efficient ammonolysis of several multinitrobenzenes to the corresponding nitroanilines was achieved by aqueous ammonia. o-Dinitrobenzene on reaction with 8 equiv. of ammonia produce the o-nitroaniline in yields of 87%. Similar reactions with p-dinitrobenzene, m-dinitrobenzene, and trinitrobenzene produce p-nitroaniline, m-nitroaniline, and 3,5-dinitroaniline, in yields of 86%, 45%, and 84%, respectively.

ACKNOWLEDGMENTS

We gratefully acknowledge the funding support by grants from the National Natural Science Foundation of China (No. 20776127), the National Key Technology R&D Program (No. 2007BA134B07), and the Opening Foundation of Zhejiang Provincial Top Key Discipline (No. 56310101613).

Notes

a Entry 1: 1H NMR (CDCl3, 400 MHz): δ6.64 (2H, s), 6.71 (2H, s), 7.97 (2H, s); Entry 2: 1H NMR (DMSO, 400 MHz): δ6.53 (2H, s), 7.73 (2H, s), 7.88 (1H, s); Entry 3: 1H NMR (CDCl3, 400 MHz): δ4.0 (2H, s), 6.95 (1H, t, J = 6.8 Hz), 7.26 (1H, t, J = 7.5 Hz), 7.48 (1H, t, J = 7.0 Hz), 7.54 (1H, t, J = 7.2 Hz).

b Isolated yield.

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