Sodium Hydroxide → HCID 23706989, compound

HRID 2418364Notes

Reaction equation

HRID 2418364 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][C:15]([Cl:18])=[CH:14][CH:13]=3)[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][C:15]([Cl:18])=[CH:14][CH:13]=2)=[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 20446297HCID 20446297, compound

Product 1

HCID 23706989HCID 23706989, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-oxo-5-(4-chlorophenoxy)indoline (4.2 g.), sodium hydroxide (2.6 g.), dioxane (20 ml.) and water (40 ml.) was refluxed under heating for 5 days 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.) and filtered. The filtrate was washed with diethyl ether and evaporated. The residue was dissolved in ethyl acetate (200 ml.) under warming and filtered. The filtrate was cooled, and the precipitating crystals were collected by filtration, washed with ethyl acetate and then recrystallized from a mixture of ethanol and ethyl acetate to give the captioned compound (3.4 g.). mp 206° to 209° 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 water (50 ml.)
  7. filtrationfiltered
  8. washThe filtrate was washed with diethyl ether
  9. customevaporated
  10. dissolutionThe residue was dissolved in ethyl acetate (200 ml.)
  11. temperatureunder warming
  12. filtrationfiltered
  13. temperatureThe filtrate was cooled
  14. filtrationthe precipitating crystals were collected by filtration
  15. washwashed with ethyl acetate
  16. customrecrystallized from a mixture of ethanol and ethyl acetate
  17. customto give the captioned compound (3.4 g.)

Sources & evidence

ORD record
ord-3a7a6a31d2cd45c09b8b639c6af5a22c
Source dataset
uspto-grants-1984_09
Patent number
US04472433

Reaction notes

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