Phosphorus oxychloride → HCID 21891910, compound

HRID 1007868Notes

Reaction equation

HRID 1007868 reaction equation
[CH2:1]([C:3]1[C:12]2[C:7](=[CH:8][C:9]([F:15])=[C:10]([O:13][CH3:14])[CH:11]=2)[NH:6][C:5](=O)[C:4]=1[C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH3:2].P(Cl)(Cl)([Cl:24])=O>>[Cl:24][C:5]1[C:4]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:3]([CH2:1][CH3:2])[C:12]2[C:7](=[CH:8][C:9]([F:15])=[C:10]([O:13][CH3:14])[CH:11]=2)[N:6]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 21892008Ethyl 4-ethyl-7-fluoro-6-methoxy-2-oxo-1,2-dihydro-3-quinolinecarboxylate

Product 1

HCID 21891910HCID 21891910, compound

Procedure

A suspension of ethyl 4-ethyl-7-fluoro-6-methoxy-2-oxo-1,2-dihydro-3-quinolinecarboxylate (19.4 g, 0.066 mol) in phosphoryl chloride (243 ml) is heated at reflux for 6 hours. The phosphoryl chloride is distilled off. The reaction mixture is decanted into ice-cooled water, then taken up in dichloromethane to solubilize. The organic phase is washed with water, then with a saturated solution of sodium chloride. The organic phase is dried over magnesium sulphate and the solvent is evaporated off. The residue is suspended in ether and the non-converted starting product (4 g) is filtered out. The filtrate is evaporated and the residue is purified by column chromatography (SiO2, AcOEt/Hpt: 5/95 to 20/80). 10.9 g of a white solid is obtained.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 6 hours
  3. distillationThe phosphoryl chloride is distilled off
  4. customThe reaction mixture is decanted into ice-
  5. temperaturecooled water
  6. washThe organic phase is washed with water
  7. dry with materialThe organic phase is dried over magnesium sulphate
  8. customthe solvent is evaporated off
  9. filtrationthe non-converted starting product (4 g) is filtered out
  10. customThe filtrate is evaporated
  11. customthe residue is purified by column chromatography (SiO2, AcOEt/Hpt: 5/95 to 20/80)

Sources & evidence

ORD record
ord-af8e918471844f68ae7b679be6ebf584
Source dataset
uspto-grants-2004_09
Patent number
US06797715B1

Reaction notes

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