Sodium Hydroxide → 5-Hydroxydiclofenac

HRID 1493498Notes

Reaction equation

HRID 1493498 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]1[C:17]2[C:12](=[CH:13][C:14]([OH:18])=[CH:15][CH:16]=2)[CH2:11][C:10]1=[O:19].[OH-:20].[Na+]>O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[NH:9][C:17]1[CH:16]=[CH:15][C:14]([OH:18])=[CH:13][C:12]=1[CH2:11][C:10]([OH:19])=[O:20]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 198137141-(2,6-Dichlorophenyl)-5-hydroxy-1,3-dihydro-2H-indol-2-one

Product 1

HCID 30525665-HydroxydiclofenacYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 1-(2,6-dichlorophenyl)-5-hydroxy-2-indolinone (2.0 g, 6.8 mmol) in 25 mL of 2.5N NaOH is heated at reflux for 2 hours. The cool reaction mixture is diluted with 20 mL of water and washed with ethyl ether. The basic layer is acidified with concentrated HCl and extracted with ethyl acetate (2×25 mL). The organic phase is washed with brine and dried (Na2SO4). Removal of solvent affords the product (2.0 g, 95%) as a brown foam (of suitable purity for use in the next step).

Workup

  1. temperatureat reflux for 2 hours
  2. customThe cool reaction mixture
  3. washwashed with ethyl ether
  4. extractionextracted with ethyl acetate (2×25 mL)
  5. washThe organic phase is washed with brine
  6. dry with materialdried (Na2SO4)
  7. customRemoval of solvent

Sources & evidence

ORD record
ord-61aa9de9996949c387cfd0392c34aa8e
Source dataset
uspto-grants-1991_06
Patent number
US05021576

Reaction notes

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