Sodium Hydroxide → HCID 20446284, compound

HRID 2418374Notes

Reaction equation

HRID 2418374 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][C:15]([Cl:18])=[CH:14][CH:13]=3)[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][C:15]([Cl:18])=[CH:14][CH:13]=2)=[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 20446189HCID 20446189, compound

Product 1

HCID 20446284HCID 20446284, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-oxo-7-(4-chloroanilino)indoline (3.2 g.), sodium hydroxide (1.2 g.), dioxane (20 ml.) and water (40 ml.) was refluxed under heating for 118 hours with stirring. After cooling, the reaction mixture was filtered and the filtrate was evaporated under reduced pressure. The residue was dissolved in water and washed with ethyl acetate, adjusted to pH 2 to 3 with 5% sulfuric acid and extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The residue was washed with benzene to give 2-[2-amino-3-(4-chloroanilino)phenyl]acetic acid (2.7 g.). mp 190° to 192° C.

Workup

  1. temperaturewas refluxed
  2. temperatureunder heating for 118 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
  7. washwashed with ethyl acetate
  8. extractionextracted with ethyl acetate
  9. washThe extract was washed with water
  10. dry with materialdried over magnesium sulfate
  11. concentrationconcentrated under reduced pressure
  12. washThe residue was washed with benzene

Sources & evidence

ORD record
ord-c71a00cad1284d4eb1dc224fd65ad507
Source dataset
uspto-grants-1984_09
Patent number
US04472433

Reaction notes

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