Phosphorus oxychloride → 4-Chloroquinoline

HRID 513729Notes

Reaction equation

HRID 513729 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](O)=[CH:3][CH:2]=1.O=P(Cl)(Cl)[Cl:14]>>[Cl:14][C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[N:1]=[CH:2][CH:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178516385quinolin-4-ol

Product 1

HCID 691404-ChloroquinolineYield 89%

Conditions

Temperature
90 °C

Procedure

POCl3 (50 ml) was added to quinolin-4-ol (5.0 g, 34.9 mmol) and the mixture was heated at 90° C. for 0.5 h. After cooling, the mixture was concentrated in vacuo. The residue was quenched with cold sat. NaHCO3 solution under cooling and the resulting aqueous phase was extracted with chloroform. The combined organic phases were washed with water, dried (Na2SO4) and concentrated in vacuo to give the title compound (5.0 g, 89%) which was used in the next step without further purification.

Workup

  1. temperatureAfter cooling
  2. concentrationthe mixture was concentrated in vacuo
  3. customThe residue was quenched with cold sat. NaHCO3 solution
  4. temperatureunder cooling
  5. extractionthe resulting aqueous phase was extracted with chloroform
  6. washThe combined organic phases were washed with water
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e30c6787ee1e4e3c811cc86f7c6086d8
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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