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Updated: Sep 15, 2025

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
A one-step strategy for synthesizing N-formanilide via benzamide activation and oxalic acid-driven reduction
Heewon Lee1, Nithin Pootheri1, Chang Woo Kim1
1Department of Chemistry, Chonnam National University, Gwangju, 61186 Republic of Korea. sunwoo@chonnam.ac.kr.
Abstract:
A one-step synthetic strategy for directly converting benzamides into N-formanilide derivatives has been developed using oxalic acid as a hydride source. This strategy involves the selective cleavage of the amide C-N bond through a reaction with sodium azide, generating a benzyl azide intermediate. This intermediate subsequently undergoes Curtius rearrangement to form an isocyanate species, which is then reduced by thermally decomposed oxalic acid, yielding the final N-formylated product. This strategy demonstrates a broad substrate scope, including various substituted benzamides and heterocyclic amides, achieving yields of up to 95%.
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