Sodium hydride → 1-(2,4-Dimethylbenzyl)-3-methyl-5-nitropyridin-2(1H)-one

HRID 598078

Reaktionsgleichung

Reaktionsgleichung von HRID 598078
[CH3:1][C:2]1[C:3](=[O:11])[NH:4][CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1.[H-].[Na+].Br[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][C:17]=1[CH3:23]>CN(C)C=O>[CH3:23][C:17]1[CH:18]=[C:19]([CH3:22])[CH:20]=[CH:21][C:16]=1[CH2:15][N:4]1[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=[C:2]([CH3:1])[C:3]1=[O:11]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 890973-Methyl-5-nitro-2-pyridoneHCID 27346041-(Bromomethyl)-2,4-dimethylbenzene

Produkt 1

HCID 672677431-(2,4-Dimethylbenzyl)-3-methyl-5-nitropyridin-2(1H)-oneAusbeute 34 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution containing 0.20 g (1.3 mmol) of 3-methyl-5-nitropyridine-2(1H)-one in 5 ml of N,N-dimethylformamide under a nitrogen atmosphere was added 0.037 g (1.6 mmol) of sodium hydride followed by 0.31 g (1.6 mmol) of 1-bromomethyl-2,4-dimethylbenzene. The reaction was allowed to stir at room temperature for 30 min., quenched with water and extracted with ethyl acetate. The organic phase was dried over magnesium sulfate. Filtration, removal of solvent and purification of the residue via biotage eluting with 25% ethyl acetate/hexanes gave 0.12 g (34%) of compound.

Aufarbeitung

  1. customquenched with water
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. filtrationFiltration, removal of solvent and purification of the residue via biotage
  5. washeluting with 25% ethyl acetate/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-5499473fac7046febb2700c5e56811d0
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07897607B2

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