Water → Methyl 5-cyanopyridine-2-carboxylate

HRID 1842199

Reaktionsgleichung

Reaktionsgleichung von HRID 1842199
Br[C:2]1[CH:3]=[CH:4][C:5]([C:8]([O:10][CH3:11])=[O:9])=[N:6][CH:7]=1.[Cu](C#N)[C:13]#[N:14].O>CN1C(=O)CCC1>[C:13]([C:2]1[CH:3]=[CH:4][C:5]([C:8]([O:10][CH3:11])=[O:9])=[N:6][CH:7]=1)#[N:14]

Komponenten

5

Edukt 3

HCID 962WaterHCID 7016458Methyl 5-bromopyridine-2-carboxylateHCID 178418260HCID 178418260, Verbindung

Produkt 1

HCID 45082467Methyl 5-cyanopyridine-2-carboxylateAusbeute 43,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
170 °C

Versuchsvorschrift

A mixture of methyl 5-bromopyridine-2-carboxylate (2.8 g) and copper cyanide (3.6 g) in NMP (30 mL) was heated with stirring at 170° C. for 1.5 hours. Water was added to the reaction solution at room temperature, and the insoluble matter was removed by filtration. The filtrate was extracted with ethyl acetate. The extract was washed with a saturated sodium chloride solution and then dried over anhydrous magnesium sulfate. The drying agent was removed by filtration and the filtrate was concentrated under reduced pressure. The resulting crude product was purified by silica gel column chromatography (ethyl acetate-heptane system) to obtain the title compound (920 mg).

Aufarbeitung

  1. temperaturewas heated
  2. customthe insoluble matter was removed by filtration
  3. extractionThe filtrate was extracted with ethyl acetate
  4. washThe extract was washed with a saturated sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe drying agent was removed by filtration
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe resulting crude product was purified by silica gel column chromatography (ethyl acetate-heptane system)

Quellen und Nachweise

ORD-Eintrag
ord-e37d97c48df7423a8ddbe82b423c4984
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08946210B2

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