Ethyl Acetate → HCID 86625685, compound

HRID 1662641Notes

Reaction equation

HRID 1662641 reaction equation
[C:1]([O:5][CH3:6])(=[O:4])[CH2:2][OH:3].[H-].[Na+].Cl[C:10]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[O:27][CH3:28])[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([Cl:19])[CH:17]=2)[NH:12][C:11]1=[O:20].CCOC(C)=O>C1COCC1.O>[Cl:19][C:16]1[CH:17]=[C:18]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11](=[O:20])[C:10]2([O:3][CH2:2][C:1]([O:5][CH3:6])=[O:4])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[O:27][CH3:28]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 66774Methyl GlycolateHCID 219059133,5-Dichloro-3-(2-methoxyphenyl)indolin-2-one

Product 1

HCID 86625685HCID 86625685, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Under nitrogen atmosphere, to a solution of 12.9 g of methyl glycolate in THF (250 ml), under room temperature, was added 3.43 g of NaH, and the reaction mixture was stirred for 10 minutes at the same temperature. Under room temperature, 22.0 g of 3,5-dichloro-3-(2-methoxyphenyl)-1,3-dihydro-2H-indol-2-one was added to the reaction solution and the reaction mixture was stirred for 10 minutes. To the reaction solution was added EtOAc and water and the mixture was stirred for 5 minutes. Liquid separation was performed, the aqueous layer was extracted with EtOAc, the combined organic layer was washed with 1 mol/L hydrochloric acid and saturated brine, then, was dried over MgSO4, the drying agent was separated by filtration, then, the solution was concentrated under reduced pressure. The obtained residue was purified by column chromatography (silicagel 60; mobile phase: EtOAc) to obtain 9.30 g of an orange solid. The obtained solid was crystallized from Et2O to obtain 8.18 g of the title compound (pale yellow crystal).

Workup

  1. stirringthe reaction mixture was stirred for 10 minutes
  2. stirringthe mixture was stirred for 5 minutes
  3. customLiquid separation
  4. extractionthe aqueous layer was extracted with EtOAc
  5. washthe combined organic layer was washed with 1 mol/L hydrochloric acid and saturated brine
  6. dry with materialwas dried over MgSO4
  7. customthe drying agent was separated by filtration
  8. concentrationthe solution was concentrated under reduced pressure
  9. customThe obtained residue was purified by column chromatography (silicagel 60; mobile phase: EtOAc)

Sources & evidence

ORD record
ord-8e2c3519eeb74b8f948a5a57c8a1df57
Source dataset
uspto-grants-2011_10
Patent number
US08030499B2

Reaction notes

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