Nitration of Indoles. IV. The Nitration of 2-Phenylindole

Wayland E Noland, Kent R. Rush, Lowell R. Smith

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38 Scopus citations

Abstract

Nitration of 2-phenylindole (1) follows the orientation rules previously established for 2-methylindole, except that trinitration has not been observed. Thus, nitration of 1 in concentrated sulfuric acid gives 5-nitro-2-phenylindole (8), while nitration of 1 in concentrated nitric acid gives 3,6-dinitro-2-phenylindole (4) and further nitration of 8 in concentrated nitric acid gives 3,5-dinitro-2-phenylindole (9). Catalytic hydrogenation of 8 gives 5-amino-2-phenylindole (12). The nitration product of 2-phenylisatogen (13) and nitric acid has been shown to be 5-nitro-2-phenylisatogen (14), an observation of interest because of the structural resemblance of 13 to the conjugate acid (15) of 1.

Original languageEnglish (US)
Pages (from-to)65-69
Number of pages5
JournalJournal of Organic Chemistry
Volume31
Issue number1
DOIs
StatePublished - Jan 1966

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