Phosphorus oxychloride → 2-Chloro-8-methylquinoline

HRID 1626425

Reaktionsgleichung

Reaktionsgleichung von HRID 1626425
[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N+:10]([O-])=[CH:9][CH:8]=[CH:7]2.P(Cl)(Cl)([Cl:15])=O>C1(C)C=CC=CC=1>[Cl:15][C:9]1[CH:8]=[CH:7][C:6]2[C:11](=[C:2]([CH3:1])[CH:3]=[CH:4][CH:5]=2)[N:10]=1

Komponenten

4

Edukt 2

HCID 24813Phosphorus oxychlorideHCID 12488418Quinoline, 8-methyl-, 1-oxide

Produkt 1

HCID 215401952-Chloro-8-methylquinolineAusbeute 81,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 8-methylquinoline 1-oxide (0.440 g, 2.764 mmol) in toluene (10 ml) was added phosphoryl trichloride (1.265 ml, 13.82 mmol), and the reaction was heated to 80° C. for 2 hours. The reaction was cooled to ambient temperature and concentrated. The crude material was taken up in EtOAc and washed with saturated sodium bicarbonate and saturated sodium chloride. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated to yield the desired compound (0.4 g, 2.252 mmol, 81.47% yield).

Aufarbeitung

  1. temperatureThe reaction was cooled to ambient temperature
  2. concentrationconcentrated
  3. washwashed with saturated sodium bicarbonate and saturated sodium chloride
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-d263980c4bda4320b5b4930f4bff2cf5
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08785445B2

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