Phosphorus oxychloride → HCID 58585853, compound

HRID 1297698Notes

Reaction equation

HRID 1297698 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]=[CH:11][C:10]([S:16]([CH3:19])(=[O:18])=[O:17])=[C:9]2O)=[O:5])[CH3:2].P(Cl)(Cl)([Cl:23])=O>>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]=[CH:11][C:10]([S:16]([CH3:19])(=[O:18])=[O:17])=[C:9]2[Cl:23])=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178468675HCID 178468675, compound

Product 1

HCID 58585853HCID 58585853, compound

Procedure

4-Hydroxy-3-methanesulfonyl-quinoline-6-carboxylic acid ethyl ester (example 61e, 15 g, 51 mmol) was dissolved in phosphorous oxychloride (450 mL). Then the reaction mixture was heated at the refluxing temperature for 6 hours. After cooling the reaction to about room temperature, the solvent was evaporated under reduced pressure. Dichloromethane was added to the residue, followed by extraction with water. The organic layers were collected, dried over sodium sulfate, filtered, and then concentrated in vacuo. Column chromatography gave 4-chloro-3-methanesulfonyl-quinoline-6-carboxylic acid ethyl ester (22 g, purity 70%). LC-MS m/e 250 (MH+).

Workup

  1. temperatureThen the reaction mixture was heated at the refluxing temperature for 6 hours
  2. temperatureAfter cooling
  3. customthe reaction to about room temperature
  4. customthe solvent was evaporated under reduced pressure
  5. additionDichloromethane was added to the residue
  6. extractionfollowed by extraction with water
  7. customThe organic layers were collected
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-812d320f591047cfaa3928252282a55a
Source dataset
uspto-grants-2007_07
Patent number
US07250515B2

Reaction notes

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