Sodium Hydroxide → (2-Benzoyl-4,5-dichloro-1 H-indol-3-yl)acetic Acid

HRID 396430Notes

Reaction equation

HRID 396430 reaction equation
[Cl:1][C:2]1[C:10]([Cl:11])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:12]([O:14]CC)=O)[NH:6]2.[OH-:17].[Na+]>C(O)C>[C:12]([C:5]1[NH:6][C:7]2[C:3]([C:4]=1[CH2:5][C:12]([OH:14])=[O:17])=[C:2]([Cl:1])[C:10]([Cl:11])=[CH:9][CH:8]=2)(=[O:14])[C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 4714971ethyl 4,5-dichloro-1H-indole-2-carboxylate

Product 1

HCID 9950187(2-Benzoyl-4,5-dichloro-1 H-indol-3-yl)acetic AcidYield 94%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of ethyl 4,5-dichloroindole-2-carboxylate (Ishii et al., Chem. Pharm. Bull., 1974, 22, 1981., 1.8 g, 7.0 mmol) in ethanol (40 ml) was added 2N aqueous NaOH (10 ml) and the mixture was heated at reflux temperature for 2 h. The mixture was cooled to room temperature and concentrated. The residual solid was acidified with 2N aqueous HCl (30 ml) and extracted with diethyl ether (80 ml×2). The organic extracts were dried (MgSO4) and concentrated to give 1.5 g (94%) of the title compound as yellow solids.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux temperature for 2 h
  3. concentrationconcentrated
  4. extractionextracted with diethyl ether (80 ml×2)
  5. dry with materialThe organic extracts were dried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-4a36680f268445fcbe969501f6cc3326
Source dataset
uspto-grants-2003_08
Patent number
US06608070B1

Reaction notes

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