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 language | English (US) |
|---|---|
| Pages (from-to) | 70-77 |
| Number of pages | 8 |
| Journal | Journal of Organic Chemistry |
| Volume | 31 |
| Issue number | 1 |
| DOIs | |
| State | Published - Jan 1966 |