Sodium Hydroxide → HCID 22642542, compound

HRID 1642131Notes

Reaction equation

HRID 1642131 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:14][CH:13]2[C:21]([O:23]C)=[O:22])(=[O:11])=[O:10])=[CH:5][CH:4]=1.CO.O1CCOCC1.[OH-].[Na+]>>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([S:9]([N:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:14][CH:13]2[C:21]([OH:23])=[O:22])(=[O:11])=[O:10])=[CH:7][CH:8]=1

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 11450869HCID 11450869, compoundHCID 21966525Dioxane Methanol

Product 1

HCID 22642542HCID 22642542, compound

Procedure

Methyl 1-(4-methoxyphenylsulfonyl)indoline-2-carboxylate (47.1 g, 135.6 mmol) was dissolved in a mixture of methanol/dioxane/4 M NaOH (15/4/1,1020 ml, 203.4 mmol NaOH, 1.5 eq.), and further 4 M NaOH (153 ml, 610.2 mmol, 4.5 eq.) was added thereto. The solution was stirred overnight at room temperature and then concentrated using a rotary evaporator. Ethyl acetate was added to the residue, and the mixture was washed with 0.5 M KHSO4. The aqueous phase was extracted again with ethyl acetate, and the combined organic phases were washed with saturated NaCl solution, dried (sodium sulfate) and concentrated in vacuo. The residue was washed with diethyl ether, filtered and dried.

Workup

  1. additionwas added
  2. concentrationconcentrated
  3. customa rotary evaporator
  4. additionEthyl acetate was added to the residue
  5. washthe mixture was washed with 0.5 M KHSO4
  6. extractionThe aqueous phase was extracted again with ethyl acetate
  7. washthe combined organic phases were washed with saturated NaCl solution
  8. dry with materialdried (sodium sulfate)
  9. concentrationconcentrated in vacuo
  10. washThe residue was washed with diethyl ether
  11. filtrationfiltered
  12. customdried

Sources & evidence

ORD record
ord-67e8f1ffc252423fbba8b112ea3365d0
Source dataset
uspto-grants-2012_02
Patent number
US08119633B2

Reaction notes

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