Baeyer–Emmerling indole synthesis

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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] This reaction was discovered by Adolf von Baeyer and A. Emmerling in 1869.[2] [3]

Baeyer-Emmerling indole synthesis

Reaction mechanism[edit]

The reaction of iron powder upon o-nitrocinnamic acid first yields a substituted hydroxylamine. The intermediate hydroxylamine then condenses with the 2nd carbon on the 1-position to yield indole-2-carboxylic acid, giving off H2O in the process. This carboxylic acid can be decarboxylated to yield indole.

Baeyer-Emmerling indole reaction mechanism

Related links[edit]


  1. ^ Baeyer 5. (1997-07-30). Retrieved on 2014-01-10.
  2. ^ Chamberlain, Joseph Scudder (1921). A Textbook of Organic Chemistry. Blakiston. p. 874. 
  3. ^ Lockyer, Sir Norman (1881). "Indigo and its Artificial Production". Nature 24 (610): 227. doi:10.1038/024227c0.