Baeyer-Emmerling indole synthesis
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]
Reaction Mechanism
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-carboxylc acid, giving off H2O in the process. This carboxylic acid can be decarboxylated to yield indole.
Related links
References
- ^ http://www.pmf.ukim.edu.mk/PMF/Chemistry/reactions/baeyer5.htm
- ^ http://books.google.com/books?id=9ls6AAAAMAAJ&pg=PA874&lpg=PA874&source=bl&ots=2Hp1SVvWqK&sig=itdKjny7lu3n-bveriBB2FOlARc&hl=en&ei=QTRUSr2CMIu0sgPIoZ2PDw&sa=X&oi=book_result&ct=result&resnum=2; A textbook of Organic Chemistry; Page 874
- ^ http://books.google.com/books?id=TMMKAAAAYAAJ&pg=PA229&lpg=PA229&source=bl&ots=0-PH2kY5V3&sig=1qLFGF3QKiYQOf92ubMah9JkYlc&hl=en&ei=ZG9USqP8HI_-sQOdz_mMDw&sa=X&oi=book_result&ct=result&resnum=4