The Fischer Indole Synthesis. VI. A Non-aromatic Intermediate and a New Class of Hydroindoles1

RB Carlin, DP Carlson

Index: Carlin; Carlson Journal of the American Chemical Society, 1959 , vol. 81, p. 4673,4682

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Citation Number: 30

Abstract

2, 6-Dimethylphenylhydrazine has been prepared from 2, 6-xylidine by a much improved procedure and converted to acetophenone 2, 6-dimethylphenylhydrazone (11). Treatment of the latter with zinc chloride in nitrobenzene at 120'led to a mixture from which five products were isolated: a crystalline solid C~~ HZ~ NO~ of unknown structure (trace); 2, 6-xylidine (8%); acetophenone (trace); 2-phenyl-4, 7-dirnethylindole (111, 4%); and the chief product ...