4-Picoline N-oxide → 2-Cyano-4-methylpyridine

HRID 1166368Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1166368
[N+:1]1([O-])[CH:6]=[CH:5][C:4]([CH3:7])=[CH:3][CH:2]=1.C[Si]([C:13]#[N:14])(C)C.N12CCCN=C1CCCCC2>C1COCC1>[C:13]([C:2]1[CH:3]=[C:4]([CH3:7])[CH:5]=[CH:6][N:1]=1)#[N:14]

Komponenten

5

Edukt 3

HCID 138574-Picoline N-oxideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 82115Trimethylsilyl cyanide

Produkt 1

HCID 887392-Cyano-4-methylpyridineAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To a suspension of 4-picoline N-oxide (13.64 g, 0.124 mole) in 82 ml of THF, under an inert atmosphere, was added trimethylsilyl cyanide (20.1 ml, 0.15 mole) followed by 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) (4.4 ml, 0.028 mole). After stirring at 25° C. for 12 hours, the reaction mixture was heated to reflux. After 4.5 hours, the solvent was removed under reduced pressure and the crude sample was eluted with methylene chloride through a pad of Florisil®. The solvent was removed under reduced pressure to provide (8.7 g, 60%) of 2-cyano-4-methyl pyridine, a white crystalline solid: mp 88-89° C. Anal. Calc'd. for C7H6N2: C, 71.17; H, 5.12; N, 23.71. Found: C, 70.17; H, 5.12; N, 23.44.

Aufarbeitung

  1. temperaturethe reaction mixture was heated to reflux
  2. waitAfter 4.5 hours
  3. customthe solvent was removed under reduced pressure
  4. washthe crude sample was eluted with methylene chloride through a pad of Florisil®
  5. customThe solvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-ea0f8d45d4af46dba9f86f9227c191d5
Quelldatensatz
uspto-grants-2003_09
Patentnummer
US06613789B2

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