Abstract
The nitration of 5-chloropyrazoles with a mixture of 100% nitric acid and 65% oleum or a mixture of 60% nitric acid and polyphosphoric acid gave substituted 5-chloro-4-nitropyrazoles in 45–91% yield. The nitration of 3-aryl-5-halopyrazoles was accompanied by introduction of a nitro group into the aromatic ring. 4-Chloropyrazoles failed to undergo nitration under these conditions. The reaction of 5-chloro-1,3-dimethyl-4-nitropyrazole with ethyl cyanoacetate in DMSO in the presence of K2CO3 led to the formation of ethyl 2-cyano-2-(1,3-dimethyl-4-nitro-1H-pyrazol-5-yl)acetate.
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Original Russian Text © G.V. Bozhenkov, V.A. Savosik, L.I. Larina, A.N. Mirskova, G.G. Levkovskaya, 2006, published in Zhurnal Organicheskoi Khimii, 2006, Vol. 42, No. 6, pp. 919–924.
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Bozhenkov, G.V., Savosik, V.A., Larina, L.I. et al. Synthesis and properties of 5-chloro-4-nitropyrazoles. Russ J Org Chem 42, 901–906 (2006). https://doi.org/10.1134/S1070428006060157
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DOI: https://doi.org/10.1134/S1070428006060157