When aniline is treated with a mixture of nitric acid and sulfuric acid, the expected nitration product (para-nitroaniline) is obtained in poor yield. Instead, the major product from nitration is meta-nitroaniline. Apparently, the amino group is protonated under these acidic conditions, and the resulting ammonium group is a meta-director, rather than an ortho-para director. Propose a plausible method for converting aniline into para-nitroaniline.

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Explanation:

4-nitroaniline is a nitroaniline carrying a nitro group at position 4. It has a role as a bacterial xenobiotic metabolite.

4-Nitroaniline, p-nitroaniline or 1-amino-4-nitrobenzene is an organic compound with the formula C6H6N2O2.

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