Phosphorus oxychloride → HCID 68780328, compound

HRID 2266444Notes

Reaction equation

HRID 2266444 reaction equation
[CH3:1][O:2][C:3](=[O:27])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]2[C:7]=1[C:8](=O)[C:9]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=1)=[C:10]([CH3:17])[NH:11]2.C([O-])(=O)C.[Na+].P(Cl)(Cl)([Cl:35])=O>>[CH3:1][O:2][C:3](=[O:27])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]2[C:7]=1[C:8]([Cl:35])=[C:9]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=1)[C:10]([CH3:17])=[N:11]2

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 517045Sodium AcetateHCID 68782520HCID 68782520, compound

Product 1

HCID 68780328HCID 68780328, compound

Procedure

A solution of [8-chloro-3-(4-chlorobenzyl)-2-methyl-4-oxo-1,4-dihydroquinolin-5-yloxy]acetic acid methyl ester (0.13 g) in phosphorus oxychloride (5.0 mL) was heated at 180° C. in a microwave reactor for 15 minutes. The mixture was poured into ice and the pH of the solution adjusted to 3 by the addition of sodium acetate. The mixture was extracted with ethyl acetate and the combined extracts washed with saturated aqueous sodium hydrogen carbonate solution and dried over magnesium sulfate. The solvent removed under reduced pressure to afford title compound as a beige solid, 0.12 g.

Workup

  1. additionThe mixture was poured into ice
  2. extractionThe mixture was extracted with ethyl acetate
  3. washthe combined extracts washed with saturated aqueous sodium hydrogen carbonate solution
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-8c4732f1a97245f0a356e7a8dc6d6c04
Source dataset
uspto-grants-2010_12
Patent number
US07858640B2

Reaction notes

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