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

HRID 2266477Notes

Reaction equation

HRID 2266477 reaction equation
[CH3:1][O:2][C:3](=[O:14])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[C:8]([NH2:13])[CH:7]=1.C([O:17][C:18](=O)[CH:19]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([S:30]([CH3:33])(=[O:32])=[O:31])=[CH:26][CH:25]=1)[C:20](=O)[CH3:21])C.O1CCOCC1.C([O-])(=O)C.[Na+]>O>[CH3:1][O:2][C:3](=[O:14])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[C:8]2[C:7]=1[C:18](=[O:17])[C:19]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([S:30]([CH3:33])(=[O:31])=[O:32])=[CH:26][CH:25]=1)=[C:20]([CH3:21])[NH:13]2

Participants

6

Reactant 4

HCID 312751,4-DioxaneHCID 517045Sodium AcetateHCID 66717604Methyl 2-(3-amino-4-chlorophenoxy)acetateHCID 687804132-(4-methanesulfonylbenzyl)-3-oxobutyric Acid Ethyl Ester

Product 1

HCID 68783911[8-chloro-3-(4-methanesulfonylbenzyl)-2-methyl-4-oxo-1,4-dihydroquinolin-5-yloxy]acetic Acid Methyl Ester

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of (3-amino-4-chlorophenoxy)acetic acid methyl ester (0.54 g), 2-(4-methanesulfonylbenzyl)-3-oxobutyric acid ethyl ester (0.75 g), polyphosphoric acid (2.5 mL) and dioxane (10 mL) was heated at 130° C. for 20 hours. The mixture was diluted with water and the pH of this solution this solution was adjusted to 3 by the addition of sodium acetate. The resulting precipitate was collected by filtration and dried to afford title compound as a white solid, 1.0 g.

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. customdried

Sources & evidence

ORD record
ord-8904ad2a29cc482fb806b83b1371f63c
Source dataset
uspto-grants-2010_12
Patent number
US07858640B2

Reaction notes

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