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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 431844Erstellt: 25. Oktober 2026

Dimethylformamide → 5-Methylpicolinonitrile

https://huagongshe.com/reaction/431844

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktDimethylformamideHCID 6228—
EduktDichloromethaneHCID 6344—
Edukt2-Bromo-5-methylpyridineHCID 564216—
KatalysatorZinc cyanide (Zn(CN)2)HCID 11186—
KatalysatorZincHCID 23994—
KatalysatorBis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)HCID 178418228—
LösungsmittelEthyl AcetateHCID 8857—
Produkt5-MethylpicolinonitrileHCID 7418356%

Reaktionsschritte

A mixture of 2-bromo-5-methylpyridine (2.001 g, 11.63 mmol), zinc cyanide (830 mg, 7 mmol), zinc (dust, 35 mg, 0.53 mmol), [1,1′-bis(diphenylphosphino)ferrocene] dichloropalladium(II), complex with dichloromethane (1:1) (192.5 mg, 0.24 mmol) in N,N-dimethylformamide (10 mL) was heated at reflux for 16 hours. After cooling, the reaction was diluted with ethyl acetate and extracted with water and brine. The organic solution was filtered through a plug of silica gel, washing dichloromethane. Removal of the solvent in vacuo, afforded 770 mg (56%) of 5-methyl-2-cyano-pyridine.

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS06660753B2
Quelldatensatzuspto-grants-2003_12
ORD IDord-2e27af0b4bbc4ccf8085e124a9ccd2b1
Quellennotizuspto-grants-2003_12