1H-Indole-5-Carboxylic Acid → methyl 1H-indole-5-carboxylate

HRID 1067761Notes

Reaction equation

HRID 1067761 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([OH:12])=[O:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[C:13](=O)(O)[O-].[Na+]>Cl.CO>[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([O:12][CH3:13])=[O:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

4

Reactant 2

HCID 742801H-Indole-5-Carboxylic AcidHCID 516892Sodium Bicarbonate

Product 1

HCID 2737635methyl 1H-indole-5-carboxylateYield 38.6%

Reagents, catalysts & solvents 1

HCID 21893726Hydrochloride methanolSolvent

Procedure

A mixture of 1.00 g (6.21 mmol) of 5-indolecarboxylic acid and 50 ml of 10% hydrogen chloride/methanol was refluxed for 2 hours. The reaction mixture was then poured onto ice water followed by neutralization with sodium bicarbonate. The mixture was extracted three times with ethyl acetate. The combined extracts were washed with aqueous sodium bicarbonate solution. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure to give 0.42 g (38.6%) of methyl 5-indole-carboxylate.

Workup

  1. temperaturewas refluxed for 2 hours
  2. additionThe reaction mixture was then poured onto ice water
  3. extractionThe mixture was extracted three times with ethyl acetate
  4. washThe combined extracts were washed with aqueous sodium bicarbonate solution
  5. dry with materialAfter drying over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-cc9c3613868647bbb6ee4a86aa5aa683
Source dataset
uspto-grants-2001_06
Patent number
US06248772B1

Reaction notes

Loading…