Sodium Hydroxide → HCID 20446219, compound

HRID 2418358Notes

Reaction equation

HRID 2418358 reaction equation
[O:1]=[C:2]1[CH2:10][C:9]2[C:4](=[C:5]([O:11][C:12]3[CH:17]=[C:16]([O:18][CH3:19])[C:15]([O:20][CH3:21])=[C:14]([O:22][CH3:23])[CH:13]=3)[CH:6]=[CH:7][CH:8]=2)[NH:3]1.[OH-].[Na+].[O:26]1CCOCC1>O>[NH2:3][C:4]1[C:5]([O:11][C:12]2[CH:17]=[C:16]([O:18][CH3:19])[C:15]([O:20][CH3:21])=[C:14]([O:22][CH3:23])[CH:13]=2)=[CH:6][CH:7]=[CH:8][C:9]=1[CH2:10][C:2]([OH:26])=[O:1]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 20446270HCID 20446270, compound

Product 1

HCID 20446219HCID 20446219, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-oxo-7-(3,4,5-trimethoxyphenoxy)indoline (3.2 g.), sodium hydroxide (1 g.), dioxane (20 ml.) and water (20 ml.) was refluxed under heating for 36 hours with stirring. After cooling, the reaction mixture was washed with diethyl ether. Ethyl acetate was added to the aqueous solution and adjusted to pH 4.0 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. The residue was pulverized with diethyl ether to give 2-[2-amino-3-(3,4,5-trimethoxyphenoxy)phenyl]acetic acid (2.5 g.).

Workup

  1. temperaturewas refluxed
  2. temperatureunder heating for 36 hours
  3. temperatureAfter cooling
  4. washthe reaction mixture was washed with diethyl ether
  5. additionEthyl acetate was added to the aqueous solution
  6. customThe ethyl acetate layer was separated
  7. washwashed with water
  8. dry with materialdried over magnesium sulfate
  9. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-68ffd7c8cf5a4bb1b21648d120ce5648
Source dataset
uspto-grants-1984_09
Patent number
US04472433

Reaction notes

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