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

HRID 564973Notes

Reaction equation

HRID 564973 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-92606e17c4604b388c4d102f39acf991
Source dataset
uspto-grants-2001_01
Patent number
US06169107A

Reaction notes

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