Baeyer–Emmerling indole synthesis
| Baeyer–Emmerling indole synthesis | |
|---|---|
| Named after | Adolf von Baeyer Adolph Emmerling |
| Reaction type | Ring forming reaction |
The Baeyer–Emmerling indole synthesis is a method for synthesizing indole from a (substituted) ortho-nitrocinnamic acid and iron powder in strongly basic solution.[1][2] This reaction was discovered by Adolf von Baeyer and Adolph Emmerling in 1869.[3] [4]
Reaction mechanism
The reaction of iron powder with o-nitrocinnamic acid reduces the
nitro group to a nitroso. The nitrogen then condenses with a carbon on the alkene chain with loss of a molecule of water to form a ring. Decarboxylation
gives indole.
See also
- Baeyer–Drewson indigo synthesis
References
- .
- ^ Baeyer 5 Archived 2007-08-16 at the Wayback Machine. Pmf.ukim.edu.mk (1997-07-30). Retrieved on 2014-01-10.
- ^ Chamberlain, Joseph Scudder (1921). A Textbook of Organic Chemistry. Blakiston. p. 874.
- S2CID 4100142.