Potassium Carbonate → (4,5-Dichloro-1H-indol-3-yl)acetic acid

HRID 1382121Notes

Reaction equation

HRID 1382121 reaction equation
C(=O)([O-])[O-].[K+].[K+].[Cl:7][C:8]1[C:16]([Cl:17])=[CH:15][CH:14]=[C:13]2[C:9]=1[C:10]([CH2:18][C:19]([O:21]C)=[O:20])=[CH:11][NH:12]2>O.CO>[Cl:7][C:8]1[C:16]([Cl:17])=[CH:15][CH:14]=[C:13]2[C:9]=1[C:10]([CH2:18][C:19]([OH:21])=[O:20])=[CH:11][NH:12]2

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 14406773Methyl (4,5-dichloro-1H-indol-3-yl)acetate

Product 1

HCID 13419486(4,5-Dichloro-1H-indol-3-yl)acetic acidYield 72.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

An aqueous solution prepared by dissolving 120 mg of potassium carbonate in 2.5 ml of water was added to a solution of 44 mg of methyl 4,5-dichloroindole-3-acetate in 5 ml of methanol. The mixture was refluxed for 1.5 hours, after which the methanol was removed by distillation under reduced pressure, and the aqueous solution thus obtained was extracted with ethyl acetate. The aqueous phase was acidified with 1N hydrochloric acid and extracted with ethyl acetate. The ethyl acetate phase was washed with distilled water and a saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate, and the solvent was removed by distillation under reduced pressure to obtain a crude product. The crude product was purified by a silica gel thin-layer chromatography to obtain 30 mg of 4,5-dichloroindole-3-acetic acid.

Workup

  1. customAn aqueous solution prepared
  2. temperatureThe mixture was refluxed for 1.5 hours
  3. customafter which the methanol was removed by distillation under reduced pressure
  4. customthe aqueous solution thus obtained
  5. extractionwas extracted with ethyl acetate
  6. extractionextracted with ethyl acetate
  7. washThe ethyl acetate phase was washed with distilled water
  8. dry with materiala saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate
  9. customthe solvent was removed by distillation under reduced pressure
  10. customto obtain a crude product
  11. customThe crude product was purified by a silica gel thin-layer chromatography

Sources & evidence

ORD record
ord-77cb51b9a06e4850b92138c7bc0931a9
Source dataset
uspto-grants-1989_02
Patent number
US04806143

Reaction notes

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