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Synthesis 2000; 2000(2): 243-246
DOI: 10.1055/s-2000-6244
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Regioselective Dealkylation of 2-Alkoxybenzoic Acid and Its Amide Derivatives with Aliphatic Amines

Hiroyasu Nishioka* , Masaaki Nagasawa, Kiyoshi Yoshida
  • *Central Research Laboratories, ZERIA Pharmaceutical Co., Ltd., 2512-1, Oshikiri, Kohnan-Machi, Ohsato-Gun, Saitama 360-0111, Japan; Fax +81 (48) 5 39 10 72; E-mail: ken-seizai@zeria.co.jp
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Publication Date:
31 December 2000 (online)

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The methoxy group of o-anisic acid was cleaved with aliphatic amines in aprotic dipolar solvents. This cleavage reaction was especially smooth when piperazine in dimethylacetamide was used. This method was applicable to a variety of dealkylations of o-alkoxybenzoic acid and its amide derivatives with high regioselectivity.

amides - carboxylic acids - cleavage - ethers - regioselectivity - o-anisic acid