Azobisisobutyronitrile → 3-bromomethyl-7-chloro-2-oxazol-2-yl-1-phenyl-1H-quinolin-4-one

HRID 1887782

Reaktionsgleichung

Reaktionsgleichung von HRID 1887782
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:24])[C:7]([CH3:23])=[C:8]([C:18]3[O:19][CH:20]=[CH:21][N:22]=3)[N:9]2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:4][CH:3]=1.[Br:25]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Br:25][CH2:23][C:7]1[C:6](=[O:24])[C:5]2[C:10](=[CH:11][C:2]([Cl:1])=[CH:3][CH:4]=2)[N:9]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:8]=1[C:18]1[O:19][CH:20]=[CH:21][N:22]=1

Komponenten

5

Edukt 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 712081907-chloro-3-methyl-2-oxazol-2-yl-1-phenyl-1H-quinolin-4-one

Produkt 1

HCID 866757603-bromomethyl-7-chloro-2-oxazol-2-yl-1-phenyl-1H-quinolin-4-oneAusbeute 49 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

In a 250 mL round bottom flask, 7-chloro-3-methyl-2-oxazol-2-yl-1-phenyl-1H-quinolin-4-one (0.50 g, 1.48 mmol), N-bromosuccinimide (291 mg, 1.63 mmol) and 2,2′-azobisisobutyronitrile (AIBN, 36.6 mg, 0.223 mmol) were combined with carbon tetrachloride (20 mL). The mixture was heated to reflux for 2 hr. The reaction was cooled to room temperature and solids were filtered off. The mother liquor was concentrated and purified by flash chromatography using 3:2 hexane-ethyl acetate to afford 3-bromomethyl-7-chloro-2-oxazol-2-yl-1-phenyl-1H-quinolin-4-one (300 mg, 49% yield) as a white solid.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 2 hr
  3. filtrationsolids were filtered off
  4. concentrationThe mother liquor was concentrated
  5. custompurified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-460e7a69bd0147ea852d17c6e0772ee1
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08501732B2

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