Phosphorus oxychloride → 2,6-Dichloro-3-phenylquinoline

HRID 1903220Notes

Reaction equation

HRID 1903220 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=O)[C:6]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[CH:5]2.P(Cl)(Cl)([Cl:21])=O>>[Cl:21][C:7]1[C:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([Cl:1])[CH:3]=2)[N:8]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 134415366-Chloro-3-phenylquinolin-2(1H)-one

Product 1

HCID 132001902,6-Dichloro-3-phenylquinoline

Procedure

6-Chloro-3-phenylquinolin-2-one (6.7 gm.) and phosphorus oxychloride (100 ml.) were heated together under reflux for 2 hr. The reaction mixture was then poured into ice water (1000 ml.) and extracted with ethyl acetate (3×100 ml.). The ethyl acetate extract was washed with water (3×50 ml.) and dried (Na2SO4), and the solvent was evaporated. The resulting solid was crystallised from ethanol to give 2,6-dichloro-3-phenylquinoline, m.p. 147°-9°.

Workup

  1. temperatureunder reflux for 2 hr
  2. extractionextracted with ethyl acetate (3×100 ml.)
  3. extractionThe ethyl acetate extract
  4. washwas washed with water (3×50 ml.)
  5. dry with materialdried (Na2SO4)
  6. customthe solvent was evaporated
  7. customThe resulting solid was crystallised from ethanol

Sources & evidence

ORD record
ord-f705d9b40c5c449dbffd72b8e7a5c2ed
Source dataset
uspto-grants-1984_03
Patent number
US04435405

Reaction notes

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