Dimethylformamide → [8-chloro-3-(4-methanesulfonylbenzyl)-4-methyl-2-oxo-1,2-dihydroquinolin-5-yloxy]acetic Acid Methyl Ester

HRID 2266502Notes

Reaction equation

HRID 2266502 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:25])=[C:6]2[C:11]=1[NH:10][C:9](=[O:12])[C:8]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:16][CH:15]=1)=[C:7]2[CH3:24].CN(C)C=O.C(=O)([O-])[O-].[K+].[K+].[CH3:37][O:38][C:39](=[O:42])[CH2:40]Br>O.C(O)(=O)C>[CH3:37][O:38][C:39](=[O:42])[CH2:40][O:25][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[C:11]2[C:6]=1[C:7]([CH3:24])=[C:8]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([S:20]([CH3:23])(=[O:21])=[O:22])=[CH:16][CH:15]=1)[C:9](=[O:12])[NH:10]2

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 687847618-chloro-5-hydroxy-3-(4-methanesulfonylbenzyl)-4-methyl-1H-quinolin-2-one

Product 1

HCID 68780457[8-chloro-3-(4-methanesulfonylbenzyl)-4-methyl-2-oxo-1,2-dihydroquinolin-5-yloxy]acetic Acid Methyl Ester

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A mixture of 8-chloro-5-hydroxy-3-(4-methanesulfonylbenzyl)-4-methyl-1H-quinolin-2-one (0.20 g), N,N-dimethylformamide (4.0 mL), potassium carbonate (0.091 g) and bromoacetic acid methyl ester (0.079 g) was stirred at room temperature for 1 hour. The mixture was diluted with water (20 mL) and the pH adjusted to 4 by the addition of glacial acetic acid. The resulting precipitate was collected by filtration and purified by column chromatography on silica gel, eluting with a mixture of dichloromethane and ethyl acetate (1:0 to 1:1 by volume) to afford title compound as a white solid, 0.14 g.

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. custompurified by column chromatography on silica gel
  3. washeluting with a mixture of dichloromethane and ethyl acetate (1:0 to 1:1 by volume)

Sources & evidence

ORD record
ord-e49adcb0a3ae494ba6626b27ff746d69
Source dataset
uspto-grants-2010_12
Patent number
US07858640B2

Reaction notes

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