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Issue 10, 2009
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One-pot synthesis of N,N-dimethylaniline from nitrobenzene and methanol

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Abstract

A route for the direct synthesis of N,N-dimethylaniline from nitrobenzene and methanol was developed through the sequential coupling of the hydrogen production from methanol, hydrogenation of nitrobenzene to produce aniline, and N-methylation of aniline over a pretreated Raney-Ni® catalyst (at 443 K in methanol). A high yield of N,N-dimethylaniline up to 98% was obtained by the proposed methodology. In this process, aniline was produced from in-situhydrogenation of nitrobenzene with hydrogen generated from methanol, or transfer hydrogenation of nitrobenzene with methanol as donor, while methanol acted as a hydrogen source, alkylating reagent and solvent, simultaneously. Additionally, a plausible mechanism of this one-pot reaction process has been described.

Graphical abstract: One-pot synthesis of N,N-dimethylaniline from nitrobenzene and methanol

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Publication details

The article was received on 20 Mar 2009, accepted on 22 Jun 2009 and first published on 21 Jul 2009


Article type: Paper
DOI: 10.1039/B905656D
New J. Chem., 2009,33, 2051-2054

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    One-pot synthesis of N,N-dimethylaniline from nitrobenzene and methanol

    L. Xu, X. Li, Y. Zhu and Y. Xiang, New J. Chem., 2009, 33, 2051
    DOI: 10.1039/B905656D

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