Potassium Carbonate → [8-chloro-3-(4-chlorobenzyl)-2,4-dimethylquinolin-5-yloxy]acetic Acid Methyl Ester

HRID 2266421Notes

Reaction equation

HRID 2266421 reaction equation
[Cl:1][C:2]1[C:11]2[N:10]=[C:9]([CH3:12])[C:8]([CH2:13][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]([CH2:13][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 1363358958-Chloro-3-(4-chlorobenzyl)-2,4-dimethylquinolin-5-ol

Product 1

HCID 68779636[8-chloro-3-(4-chlorobenzyl)-2,4-dimethylquinolin-5-yloxy]acetic Acid Methyl Ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 8-chloro-3-(4-chlorobenzyl)-2,4-dimethylquinolin-5-ol (0.23 g), N,N-dimethylformamide (5.0 mL), potassium carbonate (0.11 g) and bromoacetic acid methyl ester (0.075 mL) was stirred at room temperature for 17 hours. The mixture was concentrated under reduced pressure and the residue diluted with ethyl acetate and this mixture was washed with saturated aqueous sodium chloride solution and then 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 (1:1 by volume) gave title compound, 0.11 g.

Workup

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

Sources & evidence

ORD record
ord-c79f712aee4e4ed690355d09be9c0928
Source dataset
uspto-grants-2010_12
Patent number
US07858640B2

Reaction notes

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