Phosphorus oxychloride → 2-Chloro-4-phenylquinoline

HRID 1789636Notes

Reaction equation

HRID 1789636 reaction equation
P(Cl)(Cl)([Cl:3])=O.O[C:7]1[CH:16]=[C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]=1>>[Cl:3][C:7]1[CH:16]=[C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178515531HCID 178515531, compound

Product 1

HCID 23066872-Chloro-4-phenylquinoline

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.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 4 hours
  3. additionthe mixture was added slowly
  4. extractionThe mixture was extracted with methylene chloride
  5. dry with materialdried with magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-384b01392825410abd4d8cdf98b1c32b
Source dataset
uspto-grants-2006_07
Patent number
US07070868B2

Reaction notes

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