Potassium Carbonate → (5,6-Dichloro-1H-indol-3-yl)acetic acid

HRID 1382122Notes

Reaction equation

HRID 1382122 reaction equation
C(=O)([O-])[O-].[K+].[K+].[Cl:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][C:16]=1[Cl:17])[NH:13][CH:12]=[C:11]2[CH2:18][C:19]([O:21]CCCC)=[O:20]>O.CO>[Cl:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][C:16]=1[Cl:17])[NH:13][CH:12]=[C:11]2[CH2:18][C:19]([OH:21])=[O:20]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 14391419Butyl (5,6-dichloro-1H-indol-3-yl)acetate

Product 1

HCID 13419487(5,6-Dichloro-1H-indol-3-yl)acetic acidYield 33.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

An aqueous solution prepared by dissolving 280 mg of potassium carbonate in 2.5 ml of water was added to a solution of 100 mg of n-butyl 5,6-dichloroindole-3-acetate in 10 ml of methanol. After 1.5 hours of refluxing, the methanol was removed from the reaction solution 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 27 mg of 5,6-dichloroindole-3-acetic acid.

Workup

  1. customAn aqueous solution prepared
  2. temperatureAfter 1.5 hours of refluxing
  3. customthe methanol was removed from the reaction solution 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-84409e038fd546e88bfdf96dc5d6b39a
Source dataset
uspto-grants-1989_02
Patent number
US04806143

Reaction notes

Loading…