Investigation of m-nitroaniline formation during the Zimmermann reaction |
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Authors: | C.S. Ho K.G. Blass |
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Affiliation: | Department of Chemistry, University of Regina, Regina, Saskatchewan, S4S 0A2 Canada |
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Abstract: | The Zimmermann reaction for the determination of 17-ketosteroids was tested under both room-temperature and steam-distillation reaction conditions. meta-Nitroaniline was isolated from the residue of the steam distillation by ether extraction and thin-layer chromatography. Conclusive identification was by infrared spectroscopy. In contrast, m-nitroaniline was not formed under room-temperature reaction conditions, even when allowed to react for 24 hr. Similar results were also obtained for the reaction between acetone and m-dinitrobenzene under alkaline conditions. In conclusion, the results indicate that m-nitroaniline formation cannot account for the conversion of structure I to structure II under room-temperature reaction conditions as investigated herein. |
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Keywords: | Address reprint requests to K. G. Blass Associate Professor Chemistry Department University of Regina Regina Saskatchewan S4S 0A2 Canada. |
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