Potassium Carbonate → HCID 66917774, compound

HRID 1817999Notes

Reaction equation

HRID 1817999 reaction equation
Br[CH2:2][C:3]([O:5][CH3:6])=[O:4].[OH:7][C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:17]=1[NH:16][C:15](=[O:18])[CH:14]=[CH:13]2.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:6][O:5][C:3](=[O:4])[CH2:2][O:7][C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:17]=1[NH:16][C:15](=[O:18])[CH:14]=[CH:13]2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 972508-hydroxyquinolin-2(1H)-one

Product 1

HCID 66917774HCID 66917774, compoundYield 53.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl bromoacetate (367 mg, 2.4 mmol) was added to a stirred mixture of 8-hydroxy-1H-quinolin-2-one [which was prepared according to literature procedure (Wang, T. C. et al, Synthesis, 1997, 87-90)], (322 mg, 2 mmol), K2CO3 (414 mg, 3 mmol) in DMF (10 ml) at room temperature. The reaction mixture was stirred at rt over night and then partitioned between dichloromethane and water. Water layer was extracted with dichloromethane (2×50 ml). The combined organic phase was washed with water (3×50 ml), brine and dried over sodium sulfate. After removal of solvent, the residue was washed with ether to give 250 mg of compound I-71.

Workup

  1. custompartitioned between dichloromethane and water
  2. extractionWater layer was extracted with dichloromethane (2×50 ml)
  3. washThe combined organic phase was washed with water (3×50 ml), brine
  4. dry with materialdried over sodium sulfate
  5. customAfter removal of solvent
  6. washthe residue was washed with ether

Sources & evidence

ORD record
ord-2195ed0d08ed4ba9854ce5d434af0ce0
Source dataset
uspto-grants-2009_10
Patent number
US07598397B2

Reaction notes

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