Dimethylformamide → 2-[8-chloro-3-(4-chlorobenzyl)-2,4-dimethylquinolin-5-yloxy]propionic Acid Methyl Ester

HRID 2266497Notes

Reaction equation

HRID 2266497 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.CN(C)C=O.C(=O)([O-])[O-].[K+].[K+].[CH3:34][O:35][C:36](=[O:40])[CH:37](Br)[CH3:38]>O>[CH3:34][O:35][C:36](=[O:40])[CH: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]([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)[CH3:38]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 95576Methyl 2-bromopropionateHCID 1363358958-Chloro-3-(4-chlorobenzyl)-2,4-dimethylquinolin-5-ol

Product 1

HCID 687793962-[8-chloro-3-(4-chlorobenzyl)-2,4-dimethylquinolin-5-yloxy]propionic Acid Methyl Ester

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 8-chloro-3-(4-chlorobenzyl)-2,4-dimethylquinolin-5-ol (0.18 g), N,N-dimethylformamide (2.0 mL), potassium carbonate (0.092 g) and 2-bromopropionic acid methyl ester (0.11 g) was stirred at room temperature for 3 hours. The mixture was diluted with water, extracted with ethyl acetate and the combined extracts washed with water and saturated aqueous sodium chloride solution and then dried over magnesium sulfate. The solvent removed under reduced pressure and the residue purified by column chromatography on silica gel, eluting with a mixture of ethyl acetate and cyclohexane (1:9 to 1:4 by volume) to afford title compound, 0.092 g.

Workup

  1. extractionextracted with ethyl acetate
  2. washthe combined extracts washed with water and saturated aqueous sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent removed under reduced pressure
  5. customthe residue purified by column chromatography on silica gel
  6. washeluting with a mixture of ethyl acetate and cyclohexane (1:9 to 1:4 by volume)

Sources & evidence

ORD record
ord-14a596e455d94e448e3005bec90beedf
Source dataset
uspto-grants-2010_12
Patent number
US07858640B2

Reaction notes

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