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Amination of isomeric bromo-1-methylnitropyrazoles

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

A method was developed for the synthesis of 5-bromo-1-methyl-4-nitropyrazole from 1-methylpyrazole. In the reaction with 25% aqueous ammonia at 180–190 °C, 5-bromo-1-methyl-4-nitropyrazole is readily converted to 5-amino-1-methyl-4-nitropyrazole; the production of 4-amino-1-methyl-5-nitropyrazole from 4-bromo-1-methyl-5-nitropyrazole requires the presence of a copper catalyst; under the same conditions in the amination of 4-bromo-1-methyl-3-nitropyrazole, 4-amino-1-methyl-3-nitro- and 1-methyl-3-nitropyrazoles are formed in a 2∶3 ratio.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1672–1675, December, 1983.

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Perevalov, V.P., Baryshnenkova, L.I., Andreeva, M.A. et al. Amination of isomeric bromo-1-methylnitropyrazoles. Chem Heterocycl Compd 19, 1322–1326 (1983). https://doi.org/10.1007/BF00842842

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  • DOI: https://doi.org/10.1007/BF00842842

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