Sodium Hydroxide → HCID 20446160, compound

HRID 2418362Notes

Reaction equation

HRID 2418362 reaction equation
[O:1]=[C:2]1[CH2:10][C:9]2[C:4](=[C:5]([O:11][C:12]3[CH:13]=[CH:14][CH:15]=[C:16]4[C:20]=3[NH:19][C:18](=[O:21])[CH2:17]4)[CH:6]=[CH:7][CH:8]=2)[NH:3]1.[OH-:22].[Na+].[O:24]1CCOCC1>O>[NH2:3][C:4]1[C:9]([CH2:10][C:2]([OH:1])=[O:22])=[CH:8][CH:7]=[CH:6][C:5]=1[O:11][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]([CH2:17][C:18]([OH:21])=[O:24])[C:20]=1[NH2:19]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 20446278HCID 20446278, compound

Product 1

HCID 20446160HCID 20446160, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of bis(2-oxoindolin-7-yl)ether (2.4 g.), sodium hydroxide (1.35 g.), dioxane (10 ml.) and water (50 ml.) was refluxed under heating for 7 hours with stirring. After cooling, the reaction mixture was filtered, the filtrate was concentrated under reduced pressure. The residue was dissolved in water and washed with ethyl acetate. Ethyl acetate was added to the solution and adjusted to pH 4 to 5 with 5% sulfuric acid. The ethyl acetate layer was separated, washed with water, dried over magnesium sulfate and then evaporated under reduced pressure. The residue was washed with a mixture of ethyl acetate and diethyl ether to give bis(2-amino-3-carboxymethylphenyl)ether (1.6 g.). mp22 240° C.

Workup

  1. temperaturewas refluxed
  2. temperatureunder heating for 7 hours
  3. temperatureAfter cooling
  4. filtrationthe reaction mixture was filtered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. dissolutionThe residue was dissolved in water
  7. washwashed with ethyl acetate
  8. additionEthyl acetate was added to the solution
  9. customThe ethyl acetate layer was separated
  10. washwashed with water
  11. dry with materialdried over magnesium sulfate
  12. customevaporated under reduced pressure
  13. washThe residue was washed with a mixture of ethyl acetate and diethyl ether

Sources & evidence

ORD record
ord-56b6f2fc30a14657a12b309cce4f2ee2
Source dataset
uspto-grants-1984_09
Patent number
US04472433

Reaction notes

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