Reissert indole synthesis
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| Reissert indole synthesis | |
|---|---|
| Named after | Arnold Reissert |
| Reaction type | Ring forming reaction |
The 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]
Potassium ethoxide has been shown to give better results than sodium ethoxide.[3]
The first step of the 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.
