Pyridine → 1-Methyl-2-oxo-1,2-dihydropyridine-4-carbonitrile

HRID 1829175Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1829175
C(Cl)(=O)C(Cl)=O.CN(C)C=O.[CH3:12][N:13]1[CH:18]=[CH:17][C:16]([C:19]([NH2:21])=O)=[CH:15][C:14]1=[O:22].N1C=CC=CC=1>C(#N)C.O>[CH3:12][N:13]1[CH:18]=[CH:17][C:16]([C:19]#[N:21])=[CH:15][C:14]1=[O:22]

Komponenten

7

Edukt 4

HCID 1049PyridineHCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 8206011-Methyl-2-oxo-1,2-dihydropyridine-4-carboxamide

Produkt 1

HCID 111709951-Methyl-2-oxo-1,2-dihydropyridine-4-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel2×

Versuchsvorschrift

Oxalyl chloride (250 μl, 2.87 mmol) was added to an ice-cooled solution of N,N-dimethylformamide (243 μl, 3.14 mmol) in acetonitrile (3 ml). A suspension of 1-methyl-2-oxo-1,2-dihydro-4-pyridinecarboxamide (J.O.C. 24; 1959; 196) (201.5 mg, 1.32 mmol) and pyridine (470 μl, 5.82 mmol) in acetonitrile (20 ml) was added to the resulting white suspension, and the mixture stirred at room temperature for 18 hours. The mixture was diluted with water (20 ml), and extracted with ethyl acetate (2×100 ml). The combined organic solutions were washed with brine, dried (MgSO4) and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel using ethyl acetate:pentane (75:25), then dichloromethane:methanol (90:10) as eluants, to afford the title compound as a pale yellow solid, 112.3 mg.

Aufarbeitung

  1. additionwas added to the resulting white suspension
  2. extractionextracted with ethyl acetate (2×100 ml)
  3. washThe combined organic solutions were washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-a4cb381dbae547459de75a0728aa2f4f
Quelldatensatz
uspto-grants-2006_06
Patentnummer
US07060836B2

Notizen zur Reaktion

Wird geladen…