2-(p-메틸알릴아미노페닐)프로판산의 합성

Facile Synthesis of 2-(p-Methylallylaminophenyl)propionic Acid(Alminoprofen)

A new method for the synthesis of alminoprofen, which is a non-steroidal antiinflammatory agent, was described. Ethyl 2-phenyl-propionate(4) was prepared by Friedel-Crafts reaction of benzene with ethyl alpha-chloro-alpha(methylthio)acetate(1), followed by methylation and desulfurization of the resultant ethyl 2-(methylthio)phenylacetate(2). Ethyl 2-(p-aminophenyl)propionate(6) was obtained by nitration of (4) and successive reduction of ethyl 2-(p-nitrophenyl)propionate(5). Alminoprofen was synthesized by reaction of (6) with methallyl chloride, followed by hydrolysis of the resultant ethyl 2-(p-methylallylaminophenyl)propionate(7).