Sodium Hydroxide → HCID 23706970, compound

HRID 2418363Notes

Reaction equation

HRID 2418363 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][CH:13]=3)[CH:8]=2)[NH:3]1.[OH-].[Na+:19].[O:20]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][CH:13]=2)=[CH:8][C:9]=1[CH2:10][C:2]([O-:20])=[O:1].[Na+:19]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 18438748HCID 18438748, compound

Product 1

HCID 23706970HCID 23706970, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-oxo-5-phenoxyindoline (3.5 g.), sodium hydroxide (1.24 g), dioxane (20 ml.) and water (20 ml.) was refluxed under heating for a week with stirring. The reaction mixture was concentrated to dryness and the residue was dissolved in water (50 ml.) under heating and filtered. The filtrate was washed with diethyl ether and evaporated. The residue was dissolved in ethanol (100 ml.) under heating and filtered. The filtrate was concentrated at ordinal pressure to a volume of 30 ml. The concentrate was allowed to stand for one day at ambient temperature, and the precipitates were collected by filtration to give crystals of the captioned compound (2.5 g.). mp 239° to 242° C.

Workup

  1. temperaturewas refluxed
  2. temperatureunder heating for a week
  3. concentrationThe reaction mixture was concentrated to dryness
  4. dissolutionthe residue was dissolved in water (50 ml.)
  5. temperatureunder heating
  6. filtrationfiltered
  7. washThe filtrate was washed with diethyl ether
  8. customevaporated
  9. dissolutionThe residue was dissolved in ethanol (100 ml.)
  10. temperatureunder heating
  11. filtrationfiltered
  12. concentrationThe filtrate was concentrated at ordinal pressure to a volume of 30 ml
  13. filtrationthe precipitates were collected by filtration
  14. customto give crystals of the captioned compound (2.5 g.)

Sources & evidence

ORD record
ord-7f8b7de041824e7082a1eaf6a1b36fa3
Source dataset
uspto-grants-1984_09
Patent number
US04472433

Reaction notes

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