Baeyer–Emmerling indole synthesis
Baeyer–Emmerling indole synthesis | |
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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]
![Baeyer-Emmerling indole synthesis](https://upload.wikimedia.org/wikipedia/commons/thumb/6/69/Baeyer-Emmerling-indoolsynthese.png/300px-Baeyer-Emmerling-indoolsynthese.png)
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.
![Baeyer-Emmerling indole reaction mechanism](https://upload.wikimedia.org/wikipedia/commons/thumb/2/2e/Baeyer-Emmerling-indoolsynthese_mechanisme.png/470px-Baeyer-Emmerling-indoolsynthese_mechanisme.png)
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