Water → 6-Methoxy-2-pyridinecarbonitrile

HRID 1437208Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1437208
[Cu][C:2]#[N:3].Br[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH3:12])[N:6]=1.O.C(OCC)(=O)C>CN(C)C=O>[CH3:12][O:11][C:7]1[N:6]=[C:5]([C:2]#[N:3])[CH:10]=[CH:9][CH:8]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 2568102-Bromo-6-methoxypyridineHCID 178418546HCID 178418546, Verbindung

Produkt 1

HCID 130236446-Methoxy-2-pyridinecarbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
165 °C

Versuchsvorschrift

Copper(I) cyanide (2.68 g) was added to 2-bromo-6-methoxypyridine (5.62 g) in N,N-dimethylformamide (112 mL) at room temperature, followed by stirring at 165° C. for 15 hours. The resultant mixture was cooled in air. Water and ethyl acetate was added to the mixture. The insoluble matter that was formed in the mixture was filtered by Celite. The filtrate was partitioned between water and ethyl acetate. The organic layer was dried over sodium sulfate anhydrate, followed by filtration. The solvent was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography (hexane-ethyl acetate), to thereby give the title compound as a solid substance (1.78 g, 44%).

Aufarbeitung

  1. customThe insoluble matter that was formed in the mixture
  2. filtrationwas filtered by Celite
  3. customThe filtrate was partitioned between water and ethyl acetate
  4. dry with materialThe organic layer was dried over sodium sulfate anhydrate
  5. filtrationfollowed by filtration
  6. customThe solvent was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-1693acca8ef3476680cd75e42a9e8446
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07622471B2

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