Phosphorus oxychloride → 4,7-Dichloroquinoline

HRID 563009Notes

Reaction equation

HRID 563009 reaction equation
P(Cl)(Cl)([Cl:3])=O.[Cl:6][C:7]1[CH:16]=[C:15]2[C:10]([C:11](O)=[CH:12][CH:13]=[N:14]2)=[CH:9][CH:8]=1>>[Cl:3][C:11]1[C:10]2[C:15](=[CH:16][C:7]([Cl:6])=[CH:8][CH:9]=2)[N:14]=[CH:13][CH:12]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178516426HCID 178516426, compound

Product 1

HCID 68664,7-DichloroquinolineYield 88.6%

Procedure

Phosphorus oxychloride (4 mL, 429 mmol) was added to 7-chloro-4-hydroxyquinoline 2.86 g, 15.9 mmol) in a round bottom flask equipped with a reflux condenser. The mixture was heated to reflux for 2 h, then allowed to cool to room temperature. The solution was concentrated in vacuo to a thick oil, then dumped over cracked ice. The resulting solution was neutralized with saturated NaHCO3 (aq). The slurry was filtered and washed with water. The solids were dried under vacuum, afforded 4,7-dichloroquinoline as a white solid (2.79 g, 88.5% yield).

Workup

  1. customequipped with a reflux condenser
  2. temperatureThe mixture was heated
  3. temperatureto reflux for 2 h
  4. concentrationThe solution was concentrated in vacuo to a thick oil
  5. filtrationThe slurry was filtered
  6. washwashed with water
  7. customThe solids were dried under vacuum

Sources & evidence

ORD record
ord-197c3b711eec4c0cb91a5bdb67228fcd
Source dataset
uspto-grants-2011_11
Patent number
US08067436B2

Reaction notes

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