Potassium Hydroxide → HCID 22675046, compound

HRID 1634131Notes

Reaction equation

HRID 1634131 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:13]=1[C:14]1[NH:15][C:16]2[C:21]([CH:22]=1)=[CH:20][C:19]([Cl:23])=[C:18]([Cl:24])[CH:17]=2)[C:6]([O:8]CC)=[O:7].[OH-].[K+]>CCO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:13]=1[C:14]1[NH:15][C:16]2[C:21]([CH:22]=1)=[CH:20][C:19]([Cl:23])=[C:18]([Cl:24])[CH:17]=2)[C:6]([OH:8])=[O:7]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 18677346HCID 18677346, compound

Product 1

HCID 22675046HCID 22675046, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 3-methoxy-4-(5,6-dichloro-1H-indol-2-yl)-benzoate (1 g, 2.7 mmol) was added to a solution of KOH (0.4 g, 7 mmol) in EtOH (50 ml) and the mixture was refluxed for 4 h. The solvent was concentrated and the residue was dissolved in water. The aqueous solution was acidified with HCl then extracted with AcOEt. The organic phase was washed with water, dried over MgSO4 and concentrated in vacuo yielding 0.89 g (2.6 mmol, yield 99%) of the title compound.

Workup

  1. temperaturethe mixture was refluxed for 4 h
  2. concentrationThe solvent was concentrated
  3. dissolutionthe residue was dissolved in water
  4. extractionthen extracted with AcOEt
  5. washThe organic phase was washed with water
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a2370d2dd0394136bcc0801d17255069
Source dataset
uspto-grants-2003_01
Patent number
US06506758B2

Reaction notes

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