Sodium Hydroxide → HCID 20446187, compound

HRID 2418389Notes

Reaction equation

HRID 2418389 reaction equation
[O:1]=[C:2]1[CH2:10][C:9]2[C:4](=[C:5]([S:11]([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[CH:6]=[CH:7][CH:8]=2)[NH:3]1.[O:21]1CCOCC1.[OH-].[Na+]>O>[NH2:3][C:4]1[C:5]([S:11]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)(=[O:13])=[O:12])=[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 20446183HCID 20446183, compound

Product 1

HCID 20446187HCID 20446187, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-oxo-7-(4-chlorophenylsulfonyl)indoline (3.3 g) and dioxane (20 ml) was added to a solution of sodium hydroxide (2.0 g) in water (20 ml), and the mixture was refluxed with stirring for 6 hrs. The reaction mixture was concentrated in vacuo, and the residue was dissolved in water. The aqueous solution was washed with diethyl ether, adjusted to pH 4 with 5% sulfuric acid and extracted with diethyl ether. The extract was washed with saline, dried over magnesium sulfate, treated with charcoal and then evaporated in vacuo to give 2-[2-amino-3-(4-chlorophenylsulfonyl)phenyl]acetic acid (2.8 g). mp 139°-141° C.

Workup

  1. temperaturethe mixture was refluxed
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. dissolutionthe residue was dissolved in water
  4. washThe aqueous solution was washed with diethyl ether
  5. extractionextracted with diethyl ether
  6. washThe extract was washed with saline
  7. dry with materialdried over magnesium sulfate
  8. additiontreated with charcoal
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-142cceb07ff04d0988258d1a602e4842
Source dataset
uspto-grants-1984_09
Patent number
US04472433

Reaction notes

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