5-Bromo-2-methoxy-3-methylpyridine → 6-Methoxy-5-methylnicotinonitrile

HRID 1753218Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1753218
Br[C:2]1[CH:3]=[C:4]([CH3:10])[C:5]([O:8][CH3:9])=[N:6][CH:7]=1.[C:11]([Cu])#[N:12]>CN(C=O)C.CCOC(C)=O>[C:11]([C:2]1[CH:3]=[C:4]([CH3:10])[C:5]([O:8][CH3:9])=[N:6][CH:7]=1)#[N:12]

Komponenten

5

Edukt 2

HCID 225911765-Bromo-2-methoxy-3-methylpyridineHCID 178418546HCID 178418546, Verbindung

Produkt 1

HCID 534159886-Methoxy-5-methylnicotinonitrileAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 5-bromo-2-methoxy-3-methyl-pyridine (1.0 g, 5.0 mmol) in DMF (10 ml) was added CuCN (0.534 g, 6.0 mmol) and the resulting mixture is heated at reflux for 28 h. After cooling to room temperature the mixture is diluted with EtOAc and washed with 10% ammonia solution followed by water and brine solution. The organic layer was separated, dried over MgSO4 and evaporated under reduced pressure. The residue was purified by flash chromatography (5% EtOAc/Hexane) to give 5-cyano-2-methoxy-3-methyl-pyridine (36) (0.68 g, 93%).

Aufarbeitung

  1. temperaturethe resulting mixture is heated
  2. temperatureat reflux for 28 h
  3. washwashed with 10% ammonia solution
  4. customThe organic layer was separated
  5. dry with materialdried over MgSO4
  6. customevaporated under reduced pressure
  7. customThe residue was purified by flash chromatography (5% EtOAc/Hexane)

Quellen und Nachweise

ORD-Eintrag
ord-3331207347604db1bc03788b882b2c3f
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09163020B2

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