A NEW NITRATION PRODUCT, 3-NITRO-4-ACETAMIDOPHENOL, OBTAINED FROM ACETAMINOPHEN WITH NITROUS ACID

Takanobu MATSUNO; Tomoko MATSUKAWA; Yoshiharu SAKUMA; Takehisa KUNIEDA

doi:10.1248/cpb.37.1422

Takanobu MATSUNO, Tomoko MATSUKAWA, Yoshiharu SAKUMA, Takehisa KUNIEDA

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Keywords: acetaminophen, sodium nitrite, nitration, N-acetyl-p-benzoquinone imine, 3-nitro-4-acetamidophenol

JOURNAL FREE ACCESS

1989 Volume 37 Issue 5 Pages 1422-1423

DOI https://doi.org/10.1248/cpb.37.1422

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Abstract

Treatment of acetaminophen with an excess sodium nitrite under mildly acidic to neutral conditions results in smooth formation of new 3-nitro-4-acetamidophenol via N-acetyl-p-benzoquinone imine as an oxidation intermediate, which is a well-known, widely explored metabolite.

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