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Synthesis of singly 2 H‐, 3 H‐, and 14 C‐ and doubly labeled acetaminophen, phenacetin, and p‐acetanisidine

1982; Wiley; Volume: 19; Issue: 3 Linguagem: Inglês

10.1002/jlcr.2580190303

1099-1344

Kenneth K. Chan, K. Sandy Pang,

Synthesis and Biological Evaluation

Abstract Several efficient procedures for the synthesis of deuterium, tritium, and 14 C–labeled acetaminophen, phenacetin, and p‐acetanisidine are described. p‐Aminophenol was acylated by the appropriate acetic anhydride under mild conditions yielding labeled acetaminophen. With 0‐alkylation using NaCH 2 SOCH 3 and appropriate labeled and unlabeled alkyl halides, labeled phenacetin and p‐acetanisidine were also obtained. Phenacetin labeled both with 14 C on the acyl group and deuterium on the ethoxy group was synthesized in high yield by acylation of p‐phenetidine‐d 5 . The last compound was obtained by acid hydrolysis of phenacetin‐d 5 synthesized previously.