Sodium Hydroxide → HCID 15646809, compound

HRID 261508Notes

Reaction equation

HRID 261508 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][CH:14]=[CH:15][CH:16]=2)[C:11](=[O:18])[C:10]1=[O:19].[OH-:20].[Na+]>C(O)C>[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][CH:14]=[CH:13][C:12]=1[C:11](=[O:18])[C:10]([OH:19])=[O:20]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 144701461-(2,6-Dichlorophenyl)-1H-indole-2,3-dione

Product 1

HCID 15646809HCID 15646809, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 5.8 g of 1-(2,6-dichlorophenyl)indole-2,3-dione (m.p. 174°-175° C.) in 40 ml of ethanol were added 22 ml of a 1 N aqueous sodium hydroxide solution and the resulting mixture was stirred at room temperature for 1 hour. The reaction mixture was concentrated at a bath temperature of not more than 40° C. under a reduced pressure of 5 mmHg. To the residue were added 50 ml of water and the mixture was extracted with 30 ml of ether. The ether extract was separated out. The remaining aqueous layer was acidified with a 5% aqueous hydrochloric acid solution under ice-cooling and the solid thus precipitated was extracted with ether. The ether extract was washed with water and dried over sodium sulfate and concentrated at 10 mmHg without heating. The residue was recrystallized from dichloromethane-hexane to give 6.0 g of 2-(2,6-dichloroanilino)phenylglyoxylic acid as a yellow powder. m.p. 159°-159.5° C. Yield: 97% of theoretical amount

Workup

  1. concentrationThe reaction mixture was concentrated at a bath temperature of not more than 40° C. under a reduced pressure of 5 mmHg
  2. additionTo the residue were added 50 ml of water
  3. extractionthe mixture was extracted with 30 ml of ether
  4. extractionThe ether extract
  5. customwas separated out
  6. temperaturecooling
  7. customthe solid thus precipitated
  8. extractionwas extracted with ether
  9. extractionThe ether extract
  10. washwas washed with water
  11. dry with materialdried over sodium sulfate
  12. concentrationconcentrated at 10 mmHg
  13. temperaturewithout heating
  14. customThe residue was recrystallized from dichloromethane-hexane

Sources & evidence

ORD record
ord-2475dbd8a546447e9c5eba1881c05bb8
Source dataset
uspto-grants-1979_08
Patent number
US04166128

Reaction notes

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