Potassium Carbonate → [3-(4-chlorobenzyl)-2,4,7-trimethylquinolin-5-yloxy]acetic Acid Methyl Ester

HRID 2266428Notes

Reaction equation

HRID 2266428 reaction equation
[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][C:7]2[C:8]([CH3:20])=[N:9][C:10]3[CH:11]=[C:12]([CH3:19])[CH:13]=[C:14]([OH:18])[C:15]=3[C:16]=2[CH3:17])=[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:18][C:14]1[CH:13]=[C:12]([CH3:19])[CH:11]=[C:10]2[C:15]=1[C:16]([CH3:17])=[C:7]([CH2:6][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:22][CH:21]=1)[C:8]([CH3:20])=[N:9]2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 1363463303-(4-Chlorobenzyl)-2,4,7-trimethylquinolin-5-ol

Product 1

HCID 68782119[3-(4-chlorobenzyl)-2,4,7-trimethylquinolin-5-yloxy]acetic Acid Methyl Ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-(4-chlorobenzyl)-2,4,7-trimethylquinolin-5-ol (0.24 g), N,N-dimethylformamide (2.0 mL), potassium carbonate (0.12 g) and bromoacetic acid methyl ester (0.12 mL) was stirred at room temperature for 17 hours. The mixture was filtered and the filtrate concentrated under reduced pressure. The residue was triturated with diethyl ether and further purification by column chromatography on silica gel, eluting with a mixture of methyl tert-butyl ether and dichloromethane (1:4 to 3:7 by volume) gave title compound, 0.078 g.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate concentrated under reduced pressure
  3. customThe residue was triturated with diethyl ether and further purification by column chromatography on silica gel
  4. washeluting with a mixture of methyl tert-butyl ether and dichloromethane (1:4 to 3:7 by volume)

Sources & evidence

ORD record
ord-7cac65fd354b407ba80a38a300d5b050
Source dataset
uspto-grants-2010_12
Patent number
US07858640B2

Reaction notes

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