Phosphorus oxychloride → 2-Chloro-4-methyl-3-phenylquinoline

HRID 364928

Reaktionsgleichung

Reaktionsgleichung von HRID 364928
[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][C:4](=O)[C:3]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.P(Cl)(Cl)([Cl:21])=O>>[Cl:21][C:4]1[C:3]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:2]([CH3:1])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1

Komponenten

3

Edukt 2

HCID 24813Phosphorus oxychlorideHCID 6164891H-Quinolin-2-one, 4-methyl-3-phenyl-

Produkt 1

HCID 140012212-Chloro-4-methyl-3-phenylquinoline

Versuchsvorschrift

A mixture of 4-methyl-3-phenylquinolin-2-one (1.18 g.) and phosphorus oxychloride (60 ml.) was heated under reflux for 2 hr. The mixture was cooled and poured into ice-water (200 ml.), and the resulting mixture was extracted with ethyl acetate (3×50 ml.). The ethyl acetate extract was washed successively with saturated sodium carbonate solution (3×50 ml.) and water (50 ml.), dried (Na2SO4), and evaporated in vacuo to dryness. The residue was crystallised from cyclohexane to give 2-chloro-4-methyl-3-phenylquinoline, m.p. 88°-90°.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hr
  3. temperatureThe mixture was cooled
  4. extractionthe resulting mixture was extracted with ethyl acetate (3×50 ml.)
  5. extractionThe ethyl acetate extract
  6. washwas washed successively with saturated sodium carbonate solution (3×50 ml.) and water (50 ml.)
  7. dry with materialdried (Na2SO4)
  8. customevaporated in vacuo to dryness
  9. customThe residue was crystallised from cyclohexane

Quellen und Nachweise

ORD-Eintrag
ord-02857012b5304757b274d95462e798e5
Quelldatensatz
uspto-grants-1986_08
Patentnummer
US04607039

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