Methyl iodide → 1-methyl-5-nitro-2(1H)-pyridinone

HRID 1441730Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1441730
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[C:11](=O)([O-])[O-].[Cs+].[Cs+].CI>CN(C=O)C>[CH3:11][N:3]1[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]1=[O:1]

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 178526703HCID 178526703, Verbindung

Produkt 1

HCID 2958661-methyl-5-nitro-2(1H)-pyridinoneAusbeute 68,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 2-hydroxy-5-nitropyridine (600 mg, 4.28 mmol, 1 eq) in DMF (5 mL) was added cesium carbonate (1.67 g, 5.16 mmol, 1.2 eq), followed by methyl iodide (0.4 mL, 6.42 mmol, 1.5 eq). After stirring overnight, the reaction mixture was quenched with water and extracted with ethyl ether (5×20 mL). The ether was dried over Na2SO4 and concentrated under reduced pressure. The crude material was column chromatographed, eluting with 50% EtOAc/hexanes to give 450 mg of compound 50B.

Aufarbeitung

  1. customthe reaction mixture was quenched with water
  2. extractionextracted with ethyl ether (5×20 mL)
  3. dry with materialThe ether was dried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customchromatographed
  6. washeluting with 50% EtOAc/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-f82daeb7c53a4ba483d3c5949a3d4adb
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07655688B2

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