Phosphorus oxychloride → HCID 22643158, compound

HRID 2414764Notes

Reaction equation

HRID 2414764 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[C:9]([C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=1)[CH:8]=[C:7]2O)([O-:3])=[O:2].P(Cl)(Cl)([Cl:24])=O>O>[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[C:9]([C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=1)[CH:8]=[C:7]2[Cl:24])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychloride2×HCID 178526468HCID 178526468, compound

Product 1

HCID 22643158HCID 22643158, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

6-Nitro-2-(3-fluoro-phenyl)-quinolin-4-ol, 5.2 g (16.3 mmoles), was placed in a 500 mL three-neck round-bottom flask equipped with a condenser, magnetic stirrer and nitrogen inlet. To this was added 15.2 mL (25.0 g, 163 mmoles, 10 equiv.) of phosphorus oxychloride with stirring. The mixture was heated to 110° C. for 4 hr. At the end of this time the reaction was cooled to room temperature and water was cautiously added dropwise until all of the POCl3 was consumed. The product crystallised from the water and solids were collected by filtration. The solids were washed with water, placed in a 250 mL Erlenmeyer and triturated with water. After collection by filtration, washing with water, and drying in a vacuum oven, 4.6 g (84%) of the product was obtained.

Workup

  1. customequipped with a condenser, magnetic stirrer and nitrogen inlet
  2. temperatureAt the end of this time the reaction was cooled to room temperature
  3. customwas consumed
  4. customThe product crystallised from the water and solids
  5. filtrationwere collected by filtration
  6. washThe solids were washed with water
  7. customtriturated with water
  8. customAfter collection
  9. filtrationby filtration
  10. washwashing with water
  11. customdrying in a vacuum oven

Sources & evidence

ORD record
ord-437d8b53cdaa4f1796c54a5e7976cb23
Source dataset
uspto-grants-2004_11
Patent number
US06815447B2

Reaction notes

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