Synthesis of 9-Aminoanthracene by Zn/NH₄Cl-Mediated Reduction of 9-Nitroanthracene: Effect of Reaction Medium
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Shadieva G. K., Nurmonov S. E.
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The reduction of 9-nitroanthracene to 9-aminoanthracene using a Zn/NH₄Cl system was investigated with particular emphasis on the influence of the reaction medium. The reduction was examined in water, 70% aqueous ethanol, and 70% aqueous acetic acid. No appreciable conversion of 9-nitroanthracene was detected in water, whereas the use of 70% aqueous ethanol and 70% aqueous acetic acid afforded 9-aminoanthracene in yields of 38% and 77%, respectively. In the aqueous acetic acid medium, essentially complete consumption of the starting material was achieved within 45 min. After isolation and purification, 9-aminoanthracene was obtained in 78% yield with a melting point of 169–171 °C. FTIR spectroscopy showed characteristic N–H stretching bands at 3389.65 and 3238.33 cm⁻¹, together with absorption bands associated with the anthracene aromatic framework. The results demonstrate that reaction-medium composition substantially affects substrate conversion and product formation in the Zn/NH₄Cl-mediated reduction of 9-nitroanthracene.
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Authors
Shadieva G. K., Nurmonov S. E.
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References:
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