Phosphorus oxychloride → 4-Chloro-6-fluoroquinoline

HRID 638279Notes

Reaction equation

HRID 638279 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[C:5]2O.P(Cl)(Cl)([Cl:15])=O>>[Cl:15][C:5]1[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([F:1])[CH:3]=2)[N:8]=[CH:7][CH:6]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178516423HCID 178516423, compound

Product 1

HCID 27365864-Chloro-6-fluoroquinoline

Procedure

A mixture of 52 g (0.319 mol) of 6-fluoro-4-hydroxyquinoline and 100 ml of phosphorus oxychloride was stirred and heated under reflux for 3 hr. The reaction mixture was concentrated in vacuo. A slurry of the residue in methylene chloride was poured into ice-water, and the mixture neutralized with 3N sodium hydroxide. The organic phase was separated, and the aqueous phase was extracted with 250 ml of methylene chloride twice. The organic phases were combined, washed with water, dired over sodium sulfate, and concentrated in vacuo. The residue was crystallized from hexane to give 27.95 g of product, mp 71°-74°.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 3 hr
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. additionA slurry of the residue in methylene chloride was poured into ice-water
  5. customThe organic phase was separated
  6. extractionthe aqueous phase was extracted with 250 ml of methylene chloride twice
  7. washwashed with water
  8. concentrationconcentrated in vacuo
  9. customThe residue was crystallized from hexane

Sources & evidence

ORD record
ord-9246968d547d49439aba6f2b4f69d835
Source dataset
uspto-grants-1985_12
Patent number
US04560692

Reaction notes

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