Dimethylformamide → [2-chloro-3-(4-chlorobenzyl)-4,7-dimethylquinolin-5-yloxy]acetic Acid Methyl Ester

HRID 2266633Notes

Reaction equation

[Cl:1][C:2]1[C:11]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)=[C:10]([CH3:20])[C:9]2[C:8]([OH:21])=[CH:7][C:6]([CH3:22])=[CH:5][C:4]=2[N:3]=1.CN(C)C=O.C(=O)([O-])[O-].[K+].[K+].[CH3:34][O:35][C:36](=[O:39])[CH2:37]Br>O>[CH3:34][O:35][C:36](=[O:39])[CH2:37][O:21][C:8]1[CH:7]=[C:6]([CH3:22])[CH:5]=[C:4]2[C:9]=1[C:10]([CH3:20])=[C:11]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=1)[C:2]([Cl:1])=[N:3]2

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 2-chloro-3-(4-chlorobenzyl)-4,7-dimethylquinolin-5-ol (1.7 g), N,N-dimethylformamide (25 mL), potassium carbonate (2.1 g) and bromoacetic acid methyl ester (1.1 g) was stirred at 60° C. overnight. The mixture was cooled to room temperature, diluted with water and the resulting precipitate collected by filtration, washed with water and then dried to afford title compound, 0.53 g.

Workup

temperatureThe mixture was cooled to room temperature
filtrationthe resulting precipitate collected by filtration
washwashed with water
customdried

Sources & evidence

ORD record: ord-d5125f381c3646228b1a33798a36b80f
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07858640B2

Reaction notes

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