Phosphorus oxychloride → 3-Butyryl-4-chloro-8-fluoroquinoline

HRID 1885169Notes

Reaction equation

HRID 1885169 reaction equation
[C:1]([C:6]1[C:15](=O)[C:14]2[C:9](=[C:10]([F:17])[CH:11]=[CH:12][CH:13]=2)[NH:8][CH:7]=1)(=[O:5])[CH2:2][CH2:3][CH3:4].P(Cl)(Cl)([Cl:20])=O>>[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[Cl:20])=[CH:13][CH:12]=[CH:11][C:10]=2[F:17])(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 103315423-butyryl-8-fluoro-4(1H)-quinolone

Product 1

HCID 104448833-Butyryl-4-chloro-8-fluoroquinoline

Procedure

3-Butyryl-8-fluoro-4(1H)-quinolone (2.7 g, 12 mmol) and phosphoryl chloride (40 ml) were heated at reflux for 3 hours. Excess phosphoryl chloride was evaporated in vacuo. the residue poured onto ice and neutralised with aqueous ammonia. Filtration and washing with water gave 3-butyryl-4-chloro-8-fluoroquinoline ((1.75 g), m.p. 57°-60°.

Workup

  1. temperatureat reflux for 3 hours
  2. customExcess phosphoryl chloride was evaporated in vacuo
  3. additionthe residue poured onto ice and neutralised with aqueous ammonia
  4. filtrationFiltration
  5. washwashing with water

Sources & evidence

ORD record
ord-0827d1bcd53440b29cbe21ef14fc5e4f
Source dataset
uspto-grants-1992_09
Patent number
US05143920

Reaction notes

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