Chemistry:Baeyer–Emmerling indole synthesis
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| 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
References
- ↑ Bayer, A.; Emmerling, A. (1869). "Synthese des indoles". Berichte der deutschen chemischen Gesellschaft 2 (1): 679–682. doi:10.1002/cber.186900201268. https://zenodo.org/record/1424980.
- ↑ Baeyer 5 . Pmf.ukim.edu.mk (1997-07-30). Retrieved on 2014-01-10.
- ↑ Chamberlain, Joseph Scudder (1921). A Textbook of Organic Chemistry. Blakiston. p. 874. https://books.google.com/books?id=9ls6AAAAMAAJ&pg=PA874.
- ↑ Lockyer, Sir Norman (1881). "Indigo and its Artificial Production". Nature 24 (610): 227–231. doi:10.1038/024227c0. Bibcode: 1881Natur..24..227H. https://books.google.com/books?id=TMMKAAAAYAAJ&pg=PA229.
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