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Reissert indole synthesisThe Reissert indole synthesis is a series of chemical reactions designed to synthesize indole or substituted-indoles (4 and 5) from ortho-nitrotoluene 1 and diethyl oxalate 2.[1][2] Additional recommended knowledgePotassium ethoxide has been shown to give better results than sodium ethoxide.[3] Reaction mechanismThe first step of the Reissert indole synthesis is the condensation of o-nitrotoluene 1 with a diethyl oxalate 2 to give ethyl o-nitrophenylpyruvate 3. The reductive cyclization of 3 with zinc in acetic acid gives indole-2-carboxylic acid 4. If desired, 4 can be decarboxylated with heat to give indole 5. References
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This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Reissert_indole_synthesis". A list of authors is available in Wikipedia. |