Chemistry of indole

5-Methoxy-3-carbethoxyindoles are nitrated primarily in the 4 position. Replacement of the methoxy group by an acetoxy group leads to a change in orientation — only the 6 isomer is obtained. In the case of the similarly constructed 5-hydroxyindoles, monosubstitution cannot be accomplished under various conditions, and only the 4,6-dinitro derivative is formed. The synthesis of the corresponding amines by reduction of the nitro compounds is described.See [1] for communication XXXVIII.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1646–1653, December, 1973.