Water → HCID 20446164, compound

HRID 2418369Notes

Reaction equation

HRID 2418369 reaction equation
[O:1]=[C:2]1[CH2:10][C:9]2[C:4](=[C:5]([S:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[O:12])[CH:6]=[CH:7][CH:8]=2)[NH:3]1.[OH-:19].[Na+].O>O1CCOCC1>[NH2:3][C:4]1[C:5]([S:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:12])=[CH:6][CH:7]=[CH:8][C:9]=1[CH2:10][C:2]([OH:19])=[O:1]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 20446292HCID 20446292, compound

Product 1

HCID 20446164HCID 20446164, compoundYield 42.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2-oxo-7-phenylsulfinylindoline (4.3 g.), sodium hydroxide (1.2 g.), water (10 ml.) and dioxane (10 ml.) was refluxed for 6 hours with stirring. The reaction mixture was evaporated under reduced pressure, and the residue was dissolved in water and washed with diethyl ether. The aqueous solution was adjusted to pH 4 with 5% sulfuric acid and extracted with diethyl ether. The extract was washed with a saturated aqueous solution of sodium chloride twice, dried over magnesium sulfate and evaporated under reduced pressure. The residue was washed with a mixture of ethanol and diisopropyl ether to give crystals of 2-(2-amino-3-phenylsulfinylphenyl)acetic acid (1.95 g.).

Workup

  1. temperaturewas refluxed for 6 hours
  2. customThe reaction mixture was evaporated under reduced pressure
  3. dissolutionthe residue was dissolved in water
  4. washwashed with diethyl ether
  5. extractionextracted with diethyl ether
  6. washThe extract was washed with a saturated aqueous solution of sodium chloride twice
  7. dry with materialdried over magnesium sulfate
  8. customevaporated under reduced pressure
  9. washThe residue was washed with a mixture of ethanol and diisopropyl ether

Sources & evidence

ORD record
ord-2065dea5faeb445e9a8822c0581f2e3c
Source dataset
uspto-grants-1984_09
Patent number
US04472433

Reaction notes

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