Journal of the American Chemical Society

The synthesis of nitro-and aminoindoles analogous to serotonin

E Shaw, DW Woolley

Index: Shaw; Woolley Journal of the American Chemical Society, 1953 , vol. 75, p. 1877,1880

Full Text: HTML

Citation Number: 22

Abstract

A number of new 3-alkyl-and 2, 3-dialkyl-nitroindoles have been prepared by Fischer rearrangement. By the use of concentrated hydrochloric acid in a biphasic system at room temperature, aldehyde p-nitrophenylhydrazones have been converted to 3-alkyl-5- nitroindoles for the first time. From 3-~-chloroethyl-5-nitroindole, 5-nitrotryptamine and related bases were obtained. Although amino indoles have been relatively unknown, a ...