Phosphorus pentachloride → HCID 15458589, compound

HRID 2270086Notes

Reaction equation

HRID 2270086 reaction equation
[CH3:1][C:2]1[C:11]([CH3:12])=[C:10](O)[C:9]2[C:4](=[C:5]([O:14][CH3:15])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.P(Cl)(Cl)(Cl)(Cl)[Cl:17]>P(Cl)(Cl)(Cl)=O>[CH3:1][C:2]1[C:11]([CH3:12])=[C:10]([Cl:17])[C:9]2[C:4](=[C:5]([O:14][CH3:15])[CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

4

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 178488806HCID 178488806, compound

Product 1

HCID 15458589HCID 15458589, compoundYield 185.7%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

2.09 g of 2,3-dimethyl-4-hydroxy-8-methoxy-quinoline, 10 ml of phosphorus oxychloride and 0.43 g of phosphorus pentachloride are introduced into a 25 ml two-necked flask fitted with a condenser. The mixture is refluxed for 1 h. The reaction medium, cooled to room temperature, is poured onto 100 g of ice and extracted with ethyl acetate (2×100 ml). The organic phases are combined, washed with saturated sodium bicarbonate solution (200 ml), dried over magnesium sulphate and concentrated. The residue is purified by column chromatography on silica (elution solvent: dichloromethane). 0.85 g (yield: 37%) of 2,3-dimethyl-4-chloro-8-methoxyquinoline is obtained—m.p.: 130° C.

Workup

  1. customfitted with a condenser
  2. temperatureThe mixture is refluxed for 1 h
  3. extractionextracted with ethyl acetate (2×100 ml)
  4. washwashed with saturated sodium bicarbonate solution (200 ml)
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated
  7. customThe residue is purified by column chromatography on silica (elution solvent: dichloromethane)

Sources & evidence

ORD record
ord-5bc40a13e5db44ff954ad1750c344801
Source dataset
uspto-grants-2001_12
Patent number
US06331549B1

Reaction notes

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