Sodium Hydroxide → 2-(2-Amino-3-benzyloxyphenyl)acetic acid

HRID 2418360Notes

Reaction equation

HRID 2418360 reaction equation
[O:1]=[C:2]1[CH2:10][C:9]2[C:4](=[C:5]([O:11][CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:6]=[CH:7][CH:8]=2)[NH:3]1.[OH-].[Na+].[O:21]1CCOCC1>O>[NH2:3][C:4]1[C:5]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:6][CH:7]=[CH:8][C:9]=1[CH2:10][C:2]([OH:21])=[O:1]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 217172307-Benzyloxyoxindole

Product 1

HCID 204462322-(2-Amino-3-benzyloxyphenyl)acetic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-oxo-7-benzyloxyindoline (2.15 g.), sodium hydroxide (0.84 g.), dioxane (20 ml.) and water (20 ml.) was refluxed under heating for 72 hours with stirring. After cooling, the reaction mixture was evaporated under reduced pressure. The residue was dissolved in water and the solution was washed with ethyl acetate. Diethyl ether was added to the solution and adjusted to pH 4 to 5 with 5% sulfuric acid. The diethyl ether layer was separated, washed with water, dried over magnesium sulfate and then evaporated under reduced pressure. The residue was crystallized with a mixture of ethyl acetate and n-hexane to give 2-(2-amino-3-benzyloxyphenyl)acetic acid (2.2 g.).

Workup

  1. temperaturewas refluxed
  2. temperatureunder heating for 72 hours
  3. temperatureAfter cooling
  4. customthe reaction mixture was evaporated under reduced pressure
  5. dissolutionThe residue was dissolved in water
  6. washthe solution was washed with ethyl acetate
  7. additionDiethyl ether was added to the solution
  8. customThe diethyl ether layer was separated
  9. washwashed with water
  10. dry with materialdried over magnesium sulfate
  11. customevaporated under reduced pressure
  12. customThe residue was crystallized with a mixture of ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-a14f629c42a74624b27b6149c939d6ff
Source dataset
uspto-grants-1984_09
Patent number
US04472433

Reaction notes

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