Sodium Hydroxide → HCID 20446269, compound

HRID 2418367Notes

Reaction equation

HRID 2418367 reaction equation
[O:1]=[C:2]1[CH2:10][C:9]2[C:4](=[C:5]([O:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[F:19])[CH:6]=[C:7]([Cl:11])[CH:8]=2)[NH:3]1.[OH-].[Na+].[O:22]1CCOCC1>O>[NH2:3][C:4]1[C:5]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[F:19])=[CH:6][C:7]([Cl:11])=[CH:8][C:9]=1[CH2:10][C:2]([OH:22])=[O:1]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 20446157HCID 20446157, compound

Product 1

HCID 20446269HCID 20446269, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-oxo-5-chloro-7-(2-fluorophenoxy)indoline (4.0 g.), sodium hydroxide (1.2 g.), dioxane (25 ml.) and water (25 ml.) was refluxed under heating for 15 hours with stirring. The reaction mixture was evaporated under reduced pressure, and the residue was dissolved in water (200 ml.), washed with diethyl ether twice (200 ml. and 100 ml.) and then filtered. To the filtrate was added a mixture of diethyl ether (200 ml.) and ethyl acetate (200 ml.) and the mixture was adjusted to pH 4 with 5% sulfuric acid. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride (200 ml.), dried over magnesium sulfate and then evaporated under reduced pressure. The resultant product was recrystallized from ethanol (30 ml.) to give 2-[2-amino-3-(2-fluorophenoxy)-5-chlorophenyl]acetic acid (2.7 g.), mp 154° to 156° C. Thus obtained compound was dissolved in 1N aqueous sodium hydroxide (9.13 ml.) and lyophilized to give sodium 2-[2-amino-3-(2-fluorophenoxy)-5-chlorophenyl]acetate (3.15 g.). mp>250° C.

Workup

  1. temperaturewas refluxed
  2. temperatureunder heating for 15 hours
  3. customThe reaction mixture was evaporated under reduced pressure
  4. dissolutionthe residue was dissolved in water (200 ml.)
  5. washwashed with diethyl ether twice (200 ml. and 100 ml.)
  6. filtrationfiltered
  7. additionTo the filtrate was added
  8. additiona mixture of diethyl ether (200 ml.) and ethyl acetate (200 ml.)
  9. customThe organic layer was separated
  10. washwashed with a saturated aqueous solution of sodium chloride (200 ml.)
  11. dry with materialdried over magnesium sulfate
  12. customevaporated under reduced pressure
  13. customThe resultant product was recrystallized from ethanol (30 ml.)

Sources & evidence

ORD record
ord-197436bb3b9343daa7f26cd202f9a4c6
Source dataset
uspto-grants-1984_09
Patent number
US04472433

Reaction notes

Loading…