Sodium Hydroxide → HCID 23706988, compound

HRID 2418365Notes

Reaction equation

HRID 2418365 reaction equation
[O:1]=[C:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[Cl:18])[CH:8]=2)[NH:3]1.[OH-].[Na+:20].[O:21]1CCOCC1>O>[NH2:3][C:4]1[CH:5]=[CH:6][C:7]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[Cl:18])=[CH:8][C:9]=1[CH2:10][C:2]([O-:21])=[O:1].[Na+:20]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 20446286HCID 20446286, compound

Product 1

HCID 23706988HCID 23706988, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-oxo-5-(2-chlorophenoxy)indoline (3.2 g.), sodium hydroxide (2 g.), dioxane (20 ml.) and water (40 ml.) was refluxed under heating for 5 days with stirring. After cooling, the reaction mixture was filtered. The filtrate was evaporated under reduced pressure. The residue was dissolved in ethyl acetate under warming and filtered. The filtrate was cooled in an ice bath and the precipitating crystals were collected by filtration, washed with ethyl acetate and then recrystallized from a mixture of methanol and ethyl acetate to give the captioned compound (3.2 g.). mp 105° to 115° C.

Workup

  1. temperaturewas refluxed
  2. temperatureunder heating for 5 days
  3. temperatureAfter cooling
  4. filtrationthe reaction mixture was filtered
  5. customThe filtrate was evaporated under reduced pressure
  6. dissolutionThe residue was dissolved in ethyl acetate
  7. temperatureunder warming
  8. filtrationfiltered
  9. temperatureThe filtrate was cooled in an ice bath
  10. filtrationthe precipitating crystals were collected by filtration
  11. washwashed with ethyl acetate
  12. customrecrystallized from a mixture of methanol and ethyl acetate
  13. customto give the captioned compound (3.2 g.)

Sources & evidence

ORD record
ord-6117578c1ffd44e7a1f7fd1aafa65315
Source dataset
uspto-grants-1984_09
Patent number
US04472433

Reaction notes

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