Phosphorus oxychloride → 4-Chloro-6-fluoro-2-phenylquinoline

HRID 638272Notes

Reaction equation

HRID 638272 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH:6]=[C:5]2O.P(Cl)(Cl)([Cl:21])=O>>[Cl:21][C:5]1[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([F:1])[CH:3]=2)[N:8]=[C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178515554HCID 178515554, compound

Product 1

HCID 136038964-Chloro-6-fluoro-2-phenylquinoline

Procedure

A mixture of 30.4 g (0.127 mol) of 6-fluoro-2-phenyl-4-quinolinol, and 65 ml of phosphorus oxychloride was stirred and heated under reflux for 2 hr. This mixture was concentrated in vacuo, diluted with methylene chloride, and poured onto ice. The aqueous phase was neutralized with 3N sodium hydroxide. The organic phase was separated, and the aqueous phase extracted with methylene chloride. The organic phases were combined, washed with water and with brine, dried over sodium sulfate, and concentrated in vacuo to leave 34.8 g of residue. This was dissolved in methylene chloride, and the solution filtered through a plug of alumina. Concentration of the filtrate left 23.7 g of 4-chloro-6-fluoro-2-phenylquinoline, mp 96°-99°.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 2 hr
  3. concentrationThis mixture was concentrated in vacuo
  4. additiondiluted with methylene chloride
  5. additionpoured onto ice
  6. customThe organic phase was separated
  7. extractionthe aqueous phase extracted with methylene chloride
  8. washwashed with water and with brine
  9. dry with materialdried over sodium sulfate
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-06c87b7b007c453cb432f74aa9f82ba8
Source dataset
uspto-grants-1985_12
Patent number
US04560692

Reaction notes

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