Nitration of Indoles. V. Nitration of Electronegatively Substituted Indoles. Synthesis of the Four bz,3-Dinitroindoles

Wayland E Noland, Kent R. Rush

Research output: Contribution to journalArticle

32 Scopus citations

Abstract

Nitration of 3-aeetylindole (1) and indole-3-carbonitrile (10) with concentrated nitric acid gives predominantly the 6-nitro derivatives 2 and 11, with lesser amounts of the 4-nitro derivatives 3 and 12. Nitration of 1,3-diacetylindole (6) in concentrated sulfuric acid gives a mixture containing 3-acetyl-5-nitroindole (7) and 2. The synthesis of the four bz,3-dinitroindoles is described: 3,4-dinitroindole (27) from nitration of ethyl indole-2-carboxylate (23) via ethyl 4-nitroindole-2-carboxylate (24) and the dinitro ester 25 and acid 26; 3,5-dinitroindole (20) from 5- (8) or 3-nitroindole (19), or from indole-2-carboxylic acid (16) via 3-nitroindole-2-carboxylic acid (17) and the dinitro acid 21; 3,6-dinitroindole (15) from 6-nitroindole-3-carboxaldehyde (13) or 19; and 3,7-dinitroindole (31) from ethyl 7-nitroindole-2-carboxylate (28) via the dinitro ester 29 and acid 30.

Original languageEnglish (US)
Pages (from-to)70-77
Number of pages8
JournalJournal of Organic Chemistry
Volume31
Issue number1
DOIs
StatePublished - Jan 1966

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