Ethanol → Ethyl indole-2-carboxylate

HRID 1031771Notes

Reaction equation

HRID 1031771 reaction equation
[C:1]([C:4]1[NH:5][C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2)([OH:3])=[O:2].S(=O)(=O)(O)O.[CH2:18](O)[CH3:19]>>[CH2:18]([O:2][C:1]([C:4]1[NH:5][C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2)=[O:3])[CH3:19]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 72899Indole-2-carboxylic acid

Product 1

HCID 73125Ethyl indole-2-carboxylate

Procedure

Heat 5 kg of 2-carboxyindole suspended in ethanol in the presence of sulfuric acid to boiling for 8 hours. Evaporate off the ethanol, then take up with 40 liters of ethyl acetate and wash the organic solution with an aqueous sodium hydroxide solution and dry.

Workup

  1. customEvaporate off the ethanol
  2. washwash the organic solution with an aqueous sodium hydroxide solution
  3. customdry

Sources & evidence

ORD record
ord-b5419e93a3c442829e259d29dfe2a6d8
Source dataset
uspto-grants-1990_09
Patent number
US04954640

Reaction notes

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