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Synthesis of 3-amino-4-nitropyrazoles

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

3-Bromo-1,5-dimethyl-4-nitropyrazole does not react upon heating with aqueous ammonia, while 1,5-dimethyl-3,4-dinitropyrazole under the same conditions yields 3-amino-1,5-dimethyl-4-nitropyrazole, which is formed from 3-bromo-1,5-dimethyl-4-nitropyrazole in the presence of a copper catalyst. The amination of 1-methyl-3,4-dinitropyrazole-5-carboxylic acid is accompanied by decarboxylation, which is characteristic for 4-substituted 1-methylpyrazole-5-carboxylic acids upon heating in aqueous ammonia or water.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1676–1679, December, 1983.

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Perevalov, V.P., Andreeva, M.A., Baryshnenkova, L.I. et al. Synthesis of 3-amino-4-nitropyrazoles. Chem Heterocycl Compd 19, 1326–1330 (1983). https://doi.org/10.1007/BF00842843

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  • DOI: https://doi.org/10.1007/BF00842843

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