Phosphorus oxychloride → 4-Chloro-6-methoxy-7-methyl-quinoline

HRID 228866Notes

Reaction equation

HRID 228866 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[CH3:13])[NH:9][CH:8]=[CH:7][C:6]2=O.P(Cl)(Cl)([Cl:17])=O>>[Cl:17][C:6]1[C:5]2[C:10](=[CH:11][C:12]([CH3:13])=[C:3]([O:2][CH3:1])[CH:4]=2)[N:9]=[CH:8][CH:7]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 230784266-methoxy-7-methyl-1H-quinolin-4-one

Product 1

HCID 230785384-Chloro-6-methoxy-7-methyl-quinolineYield 71%

Procedure

6-Methoxy-7-methyl-1H-quinolin-4-one (73.9 g) was added to phosphorus oxychloride (160 ml), and the mixture was heated under reflux for 2 hr. The reaction solution was cooled to room temperature, and the solvent was then removed by distillation under the reduced pressure. Chloroform and water were added to the reaction solution, and the aqueous layer was neutralized with an aqueous potassium hydroxide solution. The organic layer was washed with water and saturated brine and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, hexane was added to the residue, and the precipitated crystal was collected by filtration to give 4-chloro-6-methoxy-7-methyl-quinoline (12.7 g, yield 71%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hr
  3. customthe solvent was then removed by distillation under the reduced pressure
  4. additionChloroform and water were added to the reaction solution
  5. washThe organic layer was washed with water and saturated brine
  6. dry with materialwas dried over anhydrous sodium sulfate
  7. customThe solvent was removed by distillation under the reduced pressure, hexane
  8. additionwas added to the residue
  9. filtrationthe precipitated crystal was collected by filtration

Sources & evidence

ORD record
ord-cc0010c1c67e428fa22bd8aa7247a880
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Reaction notes

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