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Synthesis 2002(3): 0320-0322
DOI: 10.1055/s-2002-20043
DOI: 10.1055/s-2002-20043
SHORTPAPER
© Georg Thieme Verlag Stuttgart · New York
Synthesis of Methyl 5- and 6-Nitroindole-2-carboxylates by Nitration of Indoline-2-carboxylic Acid
Further Information
Received
6 November 2001
Publication Date:
28 July 2004 (online)
Publication History
Publication Date:
28 July 2004 (online)
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Abstract
Indoline-2-carboxylic acid was transformed into 6-nitroindoline-2-carboxylic acid, the methyl ester of which was easily dehydrogenated by DDQ to methyl 6-nitroindole-2-carboxylate (total yield: 67%). Methyl 5-nitroindole-2-carboxylate was obtained by the nitration of methyl 1-acetylindoline-2-carboxylate acid followed by dehydrogenation with MnO2 in toluene in 40% total yield.
Key words
methyl 5- and 6-nitroindole-2-carboxylate - indoline-indole method - indoles
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