Potassium Carbonate → HCID 68781992, compound

HRID 2266466Notes

Reaction equation

HRID 2266466 reaction equation
[Cl:1][C:2]1[C:11]2[N:10]=[C:9]([CH3:12])[C:8]([S:13][C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=3)=[C:7]([CH3:21])[C:6]=2[C:5]([OH:22])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:29][O:30][C:31](=[O:34])[CH2:32]Br>CN(C)C=O>[CH3:29][O:30][C:31](=[O:34])[CH2:32][O:22][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[C:11]2[C:6]=1[C:7]([CH3:21])=[C:8]([S:13][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=1)[C:9]([CH3:12])=[N:10]2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 136335909HCID 136335909, compound

Product 1

HCID 68781992HCID 68781992, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 8-chloro-3-(4-chlorophenylsulfanyl)-2,4-dimethylquinolin-5-ol (0.99 g), N,N-dimethylformamide (40 mL), potassium carbonate (0.60 g) and bromoacetic acid methyl ester (0.32 mL) was stirred at room temperature for 24 hours. The solvent was removed under reduced pressure and the residue diluted with water and this mixture was extracted with ethyl acetate. The combined extracts were washed with water and saturated aqueous sodium chloride solution and dried over magnesium sulfate. The solvent was removed under reduced pressure and purification of the residue by column chromatography on silica gel, eluting with a mixture of ethyl acetate and cyclohexane (1:9 by volume) gave title compound as a white solid, 0.26 g.

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionthe residue diluted with water
  3. extractionthis mixture was extracted with ethyl acetate
  4. washThe combined extracts were washed with water and saturated aqueous sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was removed under reduced pressure and purification of the residue by column chromatography on silica gel
  7. washeluting with a mixture of ethyl acetate and cyclohexane (1:9 by volume)

Sources & evidence

ORD record
ord-6b37510c2c134009bf4a2ac03c40a3e1
Source dataset
uspto-grants-2010_12
Patent number
US07858640B2

Reaction notes

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