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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M. E. C. Biffin, D. J. Brown, and O. N. Porter, J. Chem. Soc., No. 17, 2159 (1968).
M. A. Khan and B. M. Lynch, Can. J. Chem.,49, 3566 (1971).
Yu. A. Manaev, M. A. Andreeva, V. P. Perevalov, B. I. Stepanov, V. A. Dubrovskaya, and V. I. Seraya, Zh. Obshch. Khim.,52, 2592 (1982).
M. A. Andreeva, M. I. Bolotov, Sh. G. Isaev, R. Ya. Mushii, V. P. Perevalov, V. I. Seraya, and B. I. Stepanov, Zh. Obshch. Khim.,50, 2116 (1980).
K.-Ch. Chang, M. R. Grimmett, D. D. Ward, and R. T. Weavers, J. Aust. J. Chem.,32, 1727 (1979).
M. R. Grimmett and K. H. R. Lim, Aust. J. Chem.,31, 689 (1978).
I. L. Finar and G. H. Lord, J. Chem. Soc., No. 7, 3314 (1957).
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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