Aryl Hydroxylation of 3-Methylacetanilide [4-²⁽³⁾H] by Several Model Systems

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The reactions of tritiated or deuterated 3-methylacetanilide with photolysis of pyridine-N-oxide, m-chloroperbenzoic acid, photolysis of hydrogen peroxide and the Fenton or Udenfriend system has been investigated. The retention of tritium (21%) obtained on the 4-hydroxylation of 3-methylacetanilide-4-³H with pyridine-N-oxide photolysis is corresponding to the tritium retention in the enzymic hydroxylation by rat in vivo and in vitro metabolisms, and the retention value (12%) observed in the reaction with m-chloroperbenzoic acid to the results obtained in the metabolism by rat pretreated with 3, 4-benzpyrene or 3-methylcholanthrene. Isotopic hydrogen in the 3-methyl-4-hydroxyacetanilide produced from 3-methylacetanilide-4-²⁽³⁾H by Fenton or Udenfriend system was also retained. The reactions with these systems under a few conditions are presented.