Synthesis

Synthesis of 2-(3-hydroxypropyl) indol-3-acetic acid and 3-(2-hydroxyethyl) indole-2-propanoic acid by selective functional group transformations

SI Bascop, JY Laronze, J Sapi

Index: Bascop, Sophie-Isabelle; Laronze, Jean-Yves; Sapi, Janos Synthesis, 2002 , # 12 p. 1689 - 1694

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Citation Number: 9

Abstract

For the preparation of 3, the well-known Fischer indole synthesis [8] starting from the symmetrical diethyl 4-oxopimelate was chosen. Direct indolisation with phenylhydrazine hydrochloride in acidic medium led to a mixture of diester 3, phenylhydrazone 4, and pyridazinone 5, whereas a two step procedure, taking advantage of the smooth formation of pyridazinone 5, [9] followed by treatment with saturated HCl/MeOH solution at reflux, proved to be efficient (73% ...