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- Q2632831 subject Q7458901.
- Q2632831 subject Q8546973.
- Q2632831 subject Q8552031.
- Q2632831 abstract "The Madelung synthesis is a chemical reaction that produces (substituted or unsubstituted) indoles by the intramolecular cyclization of N-phenylamides using strong base at high temperature. The Madelung synthesis was reported in 1912 by Walter Madelung, when he observed that 2-phenylindole was synthesized using N-benzoyl-o-toluidine and two equivalents of sodium ethoxide in a heated, airless, reaction. Common reaction conditions include use of sodium or potassium alkoxide as base in hexane or tetrahydrofuran solvents, at temperatures ranging between 200-400 °C. A hydrolysis step is also required in the synthesis. The Madelung synthesis is important because it is one of few known reactions that produce indoles from a base-catalyzed thermal cyclization of N-acyl-o-toluidines. The overall reaction for the Madelung synthesis follows.".
- Q2632831 thumbnail Madelung_overall_paint.png?width=300.
- Q2632831 wikiPageExternalLink indacene.
- Q2632831 wikiPageExternalLink enolizable-ketone.
- Q2632831 wikiPageExternalLink Chemical-Structure.10409660.html.
- Q2632831 wikiPageWikiLink Q101487.
- Q2632831 wikiPageWikiLink Q103135.
- Q2632831 wikiPageWikiLink Q103459.
- Q2632831 wikiPageWikiLink Q134856.
- Q2632831 wikiPageWikiLink Q150440.
- Q2632831 wikiPageWikiLink Q161940.
- Q2632831 wikiPageWikiLink Q164917.
- Q2632831 wikiPageWikiLink Q186414.
- Q2632831 wikiPageWikiLink Q188777.
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- Q2632831 wikiPageWikiLink Q658.
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- Q2632831 wikiPageWikiLink Q7094.
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- Q2632831 wikiPageWikiLink Q7458901.
- Q2632831 wikiPageWikiLink Q745930.
- Q2632831 wikiPageWikiLink Q804644.
- Q2632831 wikiPageWikiLink Q818534.
- Q2632831 wikiPageWikiLink Q8546973.
- Q2632831 wikiPageWikiLink Q8552031.
- Q2632831 wikiPageWikiLink Q898552.
- Q2632831 wikiPageWikiLink Q899597.
- Q2632831 wikiPageWikiLink Q900350.
- Q2632831 wikiPageWikiLink Q902363.
- Q2632831 wikiPageWikiLink Q908086.
- Q2632831 comment "The Madelung synthesis is a chemical reaction that produces (substituted or unsubstituted) indoles by the intramolecular cyclization of N-phenylamides using strong base at high temperature. The Madelung synthesis was reported in 1912 by Walter Madelung, when he observed that 2-phenylindole was synthesized using N-benzoyl-o-toluidine and two equivalents of sodium ethoxide in a heated, airless, reaction.".
- Q2632831 label "Madelung synthesis".
- Q2632831 depiction Madelung_overall_paint.png.