Sodium Hydroxide → 2-[2-Amino-3-(2-chlorophenoxy)phenyl]propionic acid

HRID 2418356Notes

Reaction equation

HRID 2418356 reaction equation
[O:1]=[C:2]1[CH:10]([CH3:11])[C:9]2[C:4](=[C:5]([O:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[Cl:19])[CH:6]=[CH:7][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[Cl:19])=[CH:6][CH:7]=[CH:8][C:9]=1[CH:10]([CH3:11])[C:2]([OH:22])=[O:1]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 20446224HCID 20446224, compound

Product 1

HCID 204462772-[2-Amino-3-(2-chlorophenoxy)phenyl]propionic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-oxo-3-methyl-7-(2-chlorophenoxy)indoline (4 g.), sodium hydroxide (2.4 g.), dioxane (25 ml.) water (25 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. To the residue was added water and the mixture was washed with diethyl ether. Ethyl acetate was added to the aqueous solution and adjusted to pH 4 to 5 with 5% sulfuric acid. The ethyl acetate layer was separated, washed with water and dried over magnesium sulfate and the solvent was distilled off under reduced pressure to give oily 2-[2-amino-3-(2-chlorophenoxy)phenyl]propionic acid (2.4 g.). This compound was dissolved in an aqueous solution of sodium bicarbonate and filtered. The filtrate was concentrated to dryness under reduced pressure and the residue was dissolved in ethyl acetate and filtered. The filtrate was evaporated under reduced pressure, and the residue was dissolved in water and lyophilized to give light brown powder of the captioned compound (1.6 g.).

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. additionTo the residue was added water
  7. washthe mixture was washed with diethyl ether
  8. additionEthyl acetate was added to the aqueous solution
  9. customThe ethyl acetate layer was separated
  10. washwashed with water
  11. dry with materialdried over magnesium sulfate
  12. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-e991a53b7086447e80331e86db10986b
Source dataset
uspto-grants-1984_09
Patent number
US04472433

Reaction notes

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