Sodium Hydroxide → 4-Chloro-2-(4-chlorophenyl)-6-fluoroquinoline

HRID 638264Notes

Reaction equation

HRID 638264 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:17]=[C:16](O)[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([F:19])[CH:14]=3)[N:9]=2)=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:22])=O.[OH-].[Na+]>C(Cl)Cl>[Cl:22][C:16]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([F:19])[CH:14]=2)[N:9]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[CH:17]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 178515605HCID 178515605, compound

Product 1

HCID 136038954-Chloro-2-(4-chlorophenyl)-6-fluoroquinoline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 25 g (91 mmol) of 2-(4-chlorophenyl)-6-fluoro-4-hydroxyquinoline and 50 ml of phosphorus oxychloride was stirred and heated under reflux for 2 hr. It was then cooled, poured onto ice and diluted with 500 ml of methylene chloride. This mixture was then made alkaline with 3N sodium hydroxide. The organic phase was separated, and the aqueous phase was extracted with 2×200 ml of methylene chloride. The organic extracts were combined, washed with water and with brine, dried over sodium sulfate, and concentrated in vacuo. The residue was collected and washed with hexane to give 22.2 g of product as a brownish solid, mp 169°-172°.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 2 hr
  3. temperatureIt was then cooled
  4. additionpoured onto ice
  5. customThe organic phase was separated
  6. extractionthe aqueous phase was extracted with 2×200 ml of methylene chloride
  7. washwashed with water and with brine
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated in vacuo
  10. customThe residue was collected
  11. washwashed with hexane

Sources & evidence

ORD record
ord-4c0d7fdd816d4799be2895ad77fa0594
Source dataset
uspto-grants-1985_12
Patent number
US04560692

Reaction notes

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