Sodium Hydroxide → HCID 20446280, compound

HRID 2418373Notes

Reaction equation

HRID 2418373 reaction equation
[O:1]=[C:2]1[CH2:10][C:9]2[C:4](=[C:5]([NH:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[Cl:18])[CH:6]=[CH:7][CH:8]=2)[NH:3]1.[OH-].[Na+].[O:21]1CCOCC1>O>[NH2:3][C:4]1[C:5]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[Cl:18])=[CH:6][CH:7]=[CH:8][C:9]=1[CH2:10][C:2]([OH:21])=[O:1]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 20446159HCID 20446159, compound

Product 1

HCID 20446280HCID 20446280, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-oxo-7-(2-chloroanilino)indoline (5 g.), sodium hydroxide (1.25 g.), dioxane (30 ml.) and water (60 ml.) was refluxed under heating for 53 hours with stirring. After cooling, the reaction mixture was filtered and the filtrate was evaporated under reduced pressure. The residue was dissolved in water (50 ml.), washed with ethyl acetate, adjusted to pH 4 to 5 with 5% sulfuric acid and then extracted with ethyl acetate (150 ml.). The extract was evaporated under reduced pressure and the residue was subjected to column chromatography on silica gel (60 g.) and eluted with ethyl acetate to give 2-[2-amino-3-(2-chloroanilino)phenyl]acetic acid (2.4 g.). mp 230° to 232° C.

Workup

  1. temperaturewas refluxed
  2. temperatureunder heating for 53 hours
  3. temperatureAfter cooling
  4. filtrationthe reaction mixture was filtered
  5. customthe filtrate was evaporated under reduced pressure
  6. dissolutionThe residue was dissolved in water (50 ml.)
  7. washwashed with ethyl acetate
  8. extractionextracted with ethyl acetate (150 ml.)
  9. customThe extract was evaporated under reduced pressure
  10. washeluted with ethyl acetate

Sources & evidence

ORD record
ord-21a167b6823740a883125ad1350f2f15
Source dataset
uspto-grants-1984_09
Patent number
US04472433

Reaction notes

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