Phosphorus oxychloride → 4,7-Dichloroquinoline

HRID 445489Notes

Reaction equation

HRID 445489 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-f78e85397bc649918b9b530df1d708a8
Source dataset
uspto-grants-2013_07
Patent number
US08476298B2

Reaction notes

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