Reaction #1876818

Reaction equation

Phosphorus oxychloride

2-hydroxy-4-phenylquinoline

→

2-chloro-4-phenylquinoline

Conditions

Workup

1. 1
   Temperaturethe mixture was heated
2. 2
   Temperatureto reflux for 4 hours
3. 3
   workup.ADDITIONthe mixture was added slowly
4. 4
   ExtractionThe mixture was extracted with methylene chloride
5. 5
   Dryingdried with magnesium sulfate
6. 6
   Filtrationfiltered
7. 7
   Concentrationconcentrated

Procedure

Phosphorus oxychloride (37.4 mL, 402 mmol) was added to 2-hydroxy-4-phenylquinoline and the mixture was heated to reflux for 4 hours. Upon cooling to room temperature, the mixture was added slowly to stirring ice water yielding a white precipitate. The mixture was extracted with methylene chloride, and the organic phases were combined, dried with magnesium sulfate, filtered and concentrated to yield 2-chloro-4-phenylquinoline.

Source