Water → HCID 86613956, compound

HRID 1811456Notes

Reaction equation

HRID 1811456 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:15][CH:16]2[S:20][C:19](=[O:21])[NH:18][C:17]2=[O:22])=[C:7]2[C:12]=1[N:11]([CH3:13])[C:10](=[O:14])[CH:9]=[CH:8]2.Br[CH2:24][C:25]([O:27][CH3:28])=[O:26].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[CH3:28][O:27][C:25]([CH2:24][N:18]1[C:17](=[O:22])[CH:16]([CH2:15][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[C:12]3[C:7]=2[CH:8]=[CH:9][C:10](=[O:14])[N:11]3[CH3:13])[S:20][C:19]1=[O:21])=[O:26]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 86613929HCID 86613929, compound

Product 1

HCID 86613956HCID 86613956, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

350 mg of 5-(8-methoxy-1-methyl-2-oxo-1,2-dihydroquinolin-5-ylmethyl)thiazolidine-2,4-dione was dissolved in 5 ml of DMF. 0.156 ml of methyl bromoacetate and 0.25 g of potassium carbonate were added to the solution, followed by stirring at room temperature overnight. Water was added, and the mixture was extracted with methylene chloride. The organic layer was washed with saturated sodium chloride solution, and dried over sodium sulfate. After filtration, the solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography and recrystallized from methanol-acetone, giving 245 mg (57% yield) of 3-methoxycarbonylmethyl-5-(8-methoxy-1-methyl-2-oxo-1,2-dihydroquinolin-5-ylmethyl)thiazolidine-2,4-dione as white crystals.

Workup

  1. extractionthe mixture was extracted with methylene chloride
  2. washThe organic layer was washed with saturated sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. filtrationAfter filtration
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified by silica gel chromatography
  7. customrecrystallized from methanol-acetone

Sources & evidence

ORD record
ord-29b374e9eaa447eb979b306aa7d69bea
Source dataset
uspto-grants-2013_01
Patent number
US08362252B2

Reaction notes

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