Dimethylformamide → HCID 68782473, compound

HRID 2266437Notes

Reaction equation

HRID 2266437 reaction equation
[Cl:1][C:2]1[C:11]2[N:10]=[C:9]([CH3:12])[C:8]([O: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.CN(C)C=O.C(=O)([O-])[O-].[K+].[K+].[CH3:34][O:35][C:36](=[O:39])[CH2:37]Br>ClCCl>[CH3:34][O:35][C:36](=[O:39])[CH2:37][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]([O: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

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 136335928HCID 136335928, compound

Product 1

HCID 68782473HCID 68782473, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 8-chloro-3-(4-chlorophenoxy)-2,4-dimethylquinolin-5-ol (0.16 g), N,N-dimethylformamide (3.0 mL), potassium carbonate (0.20 g) and bromoacetic acid methyl ester (0.88 g) was stirred at room temperature for 15 hours. The mixture was diluted with dichloromethane, washed with water 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 dichloromethane and ethyl acetate (1:0 to 5:1 by volume) gave title compound as an off-white solid, 0.20 g.

Workup

  1. washwashed with water
  2. dry with materialdried over magnesium sulfate
  3. customThe solvent was removed under reduced pressure and purification of the residue by column chromatography on silica gel
  4. washeluting with a mixture of dichloromethane and ethyl acetate (1:0 to 5:1 by volume)

Sources & evidence

ORD record
ord-30a7d2e1ad8f44f8a48dd3df2cf01736
Source dataset
uspto-grants-2010_12
Patent number
US07858640B2

Reaction notes

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