Simplifying Nucleophilic Aromatic Substitutions: Microwave-Assisted Solvent Free Synthesis of 5-Alkylamino-2-nitroanilines

Author(s): Pedro J. Trejo-Soto, Anuar Flores-Gahona, Rafael Castillo, Alicia Hernández-Campos.

Journal Name: Current Microwave Chemistry

Volume 3 , Issue 3 , 2016

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Abstract:

Background: Substituted 2-nitroanilines are synthetic intermediates used in the synthesis of important bioactive compounds. Nucleophilic aromatic substitution reactions with activated substrates, such as substituted 5-chloro-2-nitroanilines, usually involve the use of a solvent, high pressure conditions and prolonged reaction times. We describe a simple and straightforward protocol to prepare 5-substituted 2-nitroanilines that addresses these drawbacks.

Methods: Utilizing microwave irradiation and solvent free conditions, a series of 5-alkylamino-2- nitroanilines (1-14) have been efficiently prepared by reacting 4,5-dichloro-2-nitroaniline with different primary and cyclic secondary amines.

Results: The reactions proceeded in short periods of time (5-35 min) without side products, facilitating the isolation of 1- 14 in 55-93% yields. Reactions under microwave conditions were faster than those achieved with conventional heating.

Conclusion: This simplified approach can be a suitable alternative to synthetic methods involving conventional heating. The reported methodology can be applied to generate a variety of 5-substituted 2-nitroanilines which serve as precursors to compounds of pharmaceutical interest.

Keywords: 5-Substituted 2-nitroaniline, amine, green chemistry, microwave-assisted synthesis, nucleophilic aromatic substitution, solvent-free synthesis.

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Article Details

VOLUME: 3
ISSUE: 3
Year: 2016
Page: [258 - 265]
Pages: 8
DOI: 10.2174/2213335603666151217181923
Price: $58

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