Sodium Hydroxide → 2-Oxindole-5-carboxylic acid

HRID 1857552Notes

Reaction equation

HRID 1857552 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=[O:14])[CH2:8]2)=[O:4].[OH-].[Na+]>CO>[C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=[O:14])[CH2:8]2)([OH:4])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 2773516Methyl 2,3-dihydro-2-oxo-1H-indole-5-carboxylate

Product 1

HCID 27733182-Oxindole-5-carboxylic acidYield 78%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-Methoxycarbonyl-2-oxindole (1 g) and 1 g of sodium hydroxide in 20 mL of methanol was refluxed for 3 hours. The reaction mixture was cooled and concentrated to dryness. The residue was dissolved in water and extracted twice with ethyl acetate. The aqueous layer was acidified with 6 N hydrochloric acid and the precipitated solid collected, washed with water, and dried to give 0.7 g (78%) of the title compound as an off-white solid.

Workup

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated to dryness
  3. dissolutionThe residue was dissolved in water
  4. extractionextracted twice with ethyl acetate
  5. customthe precipitated solid collected
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-e0208e94ac074543b98771bf58e7d7d5
Source dataset
uspto-grants-2000_11
Patent number
US06147106

Reaction notes

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