Sodium Hydroxide → HCID 20446199, compound

HRID 2418366Notes

Reaction equation

HRID 2418366 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[Cl: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[Cl: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 20446302HCID 20446302, compound

Product 1

HCID 20446199HCID 20446199, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-oxo-5-chloro-7-(2-chlorophenoxy)indoline (2.0 g.), sodium hydroxide (0.50 g.), dioxane (20 ml.) and water (30 ml.) was refluxed under heating for 23 hours. The reaction mixture was evaporated under reduced pressure and the residue was dissolved in water and filtered. The filtrate was washed with diethyl ether, and diethyl ether was added to the aqueous layer and adjusted to pH 5 with 1N-sulfuric acid. The diethyl ether layer was separated, washed with water, dried over magnesium sulfate and then evaporated. The residue was recrystallized from ethanol to give crystals of 2-[2-amino-3-(2-chlorophenoxy)-5-chlorophenyl]acetic acid (0.725 g.).

Workup

  1. temperaturewas refluxed
  2. temperatureunder heating for 23 hours
  3. customThe reaction mixture was evaporated under reduced pressure
  4. dissolutionthe residue was dissolved in water
  5. filtrationfiltered
  6. washThe filtrate was washed with diethyl ether, and diethyl ether
  7. additionwas added to the aqueous layer and adjusted to pH 5 with 1N-sulfuric acid
  8. customThe diethyl ether layer was separated
  9. washwashed with water
  10. dry with materialdried over magnesium sulfate
  11. customevaporated
  12. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-b617a3d75b0f4a809f799fc1ac96acdc
Source dataset
uspto-grants-1984_09
Patent number
US04472433

Reaction notes

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