116922-21-5Relevant articles and documents
THE NITRATION OF SOME PHENYL-SUBSTITUTED N-HETEROCYCLES
Hurst, Derek T.
, p. 371 - 376 (2007/10/02)
The nitration of 3-methyl-1-phenylpyrazole using nitric acid and sulfuric acid at 0 deg C gives the p-nitrophenyl isomer as the only isolated mono nitro-product 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 deg C of 4-phenylmorpholine gives 4-m-nitrophenyl- and 4-p-nitrophenylmorpholine in the ratio of about 5:1.