Ethanol → HCID 23706974, compound

HRID 2418355Notes

Reaction equation

HRID 2418355 reaction equation
C([OH:3])C.[O:4]=[C:5]1[CH2:13][C:12]2[C:7](=[C:8]([O:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:9]=[CH:10][CH:11]=2)[NH:6]1.[OH-].[Na+:22]>O>[NH2:6][C:7]1[C:8]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:9][CH:10]=[CH:11][C:12]=1[CH2:13][C:5]([O-:3])=[O:4].[Na+:22]

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 12909820HCID 12909820, compound

Product 1

HCID 23706974HCID 23706974, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of ethanol (50 ml.) and water (50 ml.) were added 2-oxo-7-phenoxyindoline (20.7 g.) and sodium hydroxide (14.8 g.). The mixture was refluxed under heating for 30 hours with stirring. After cooling, the reaction mixture was filtered and ethanol was distilled off from the filtrate. The remaining aqueous solution was adjusted to pH 8.3 with conc. hydrochloric acid and filtered. The filtrate was washed with diethyl ether and concentrated to dryness under reduced pressure. The residue was dissolved in ethanol and filtered, and the filtrate was evaporated under reduced pressure. The oily residue was crystallized with ethyl acetate. The resultant substance (17.8 g.) was dissolved in water and filtered. The filtrate was lyophilized to give powdery captioned compound (17.6 g.). mp 205° to 208° C.

Workup

  1. temperatureThe mixture was refluxed
  2. temperatureunder heating for 30 hours
  3. temperatureAfter cooling
  4. filtrationthe reaction mixture was filtered
  5. distillationethanol was distilled off from the filtrate
  6. filtrationfiltered
  7. washThe filtrate was washed with diethyl ether
  8. concentrationconcentrated to dryness under reduced pressure
  9. dissolutionThe residue was dissolved in ethanol
  10. filtrationfiltered
  11. customthe filtrate was evaporated under reduced pressure
  12. customThe oily residue was crystallized with ethyl acetate
  13. dissolutionThe resultant substance (17.8 g.) was dissolved in water
  14. filtrationfiltered
  15. customto give powdery captioned compound (17.6 g.)

Sources & evidence

ORD record
ord-fce9be56c6be4cd68688619f76d9d188
Source dataset
uspto-grants-1984_09
Patent number
US04472433

Reaction notes

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