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Paper | Regular issue | Vol 27, No. 2, 1988, pp.371-376
Published online, 1st January, 1970
DOI: 10.3987/COM-87-4317
■ The Nitration of Some Phenyl-substituted N-Heterocycles

Derek T. Hurst*

*School of Analytical and Biological Chemistry, Kingston Polytechnic, Kingston-on-Thames, KT1 2EE, U.K.

Abstract

The nitration of 3-methyl-1-phenylpyrazole using nitric acid and sulphuric acid at O°C gives the p-nitrophenyl isomer as the only isolated mono nitroproduct and 3-methyl-4-nitro-1-p-nitrophenylpyrazole as the dinitro-product. 3-Methyl- 4-phenylpyrazole gives 3-methyl-4-p-nitrophenylpyrazole with the second nitration also occurring in the phenyl ring to give 3-methyl-4-(2’,4’-dinitrophenyl)pyrazole. 2-Phenylimidazole nitrates under these conditions to give first 2-p-nitrophenylimidazole and then 4-nitro-2-p-nitrophenylimidazole whilst 4-phenylimidazole gives 4-nitro-5-p-nitrophenylimidazole readily even when the amount of nitric acid is limited to one equivalent and only traces of a mono nitro-product are found. 2-Phenylimidazoline gives solely the m-nitrophenyl isomer under the same conditions. The mixed acid nitration at 0°C of 4-phenylmorpholine gives 4-m-nitrophenyl- and 4-p-nitrophenylmorpholine in the ratio of about 5:1.