Levulinic Acid → Indole

HRID 335508Notes

Reaction equation

HRID 335508 reaction equation
Cl.F[C:3]1[CH:4]=[C:5]([NH:11]N)[C:6](OC)=[CH:7][CH:8]=1.[C:13](O)(=O)[CH2:14]CC(C)=O>C(O)(=O)C>[NH:11]1[C:5]2[C:6](=[CH:7][CH:8]=[CH:3][CH:4]=2)[CH:14]=[CH:13]1

Participants

4

Reactant 2

HCID 11579Levulinic AcidHCID 55281376Hydrazine, (5-fluoro-2-methoxyphenyl)-, hydrochloride (1:1)

Product 1

HCID 798Indole

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Condensation of hydrazine hydrochloride (2) with levulinic acid (3) in acetic acid results in the formation of two regioisomeric indole derivatives 4 and 5 in a 1:7 ratio. The major regioisomer 5 can be isolated in pure form by crystallization of the reaction mixture. Alternatively, the indole mixture can be esterified with an alcohol such as 2-trimethylsilylethanol to afford the corresponding esters that can then be separated by a number of means, for example by chromatography.

Sources & evidence

ORD record
ord-aac2f077b3c74ae2b4034b72935d9923
Source dataset
uspto-grants-2014_11
Patent number
US08884020B2

Reaction notes

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