Sodium hydride → 1-(4-Methoxybenzyl)-5-iodo-4-methyl-3-nitro-2-pyridone

HRID 1594668Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1594668
[I:1][C:2]1[C:3]([CH3:12])=[C:4]([N+:9]([O-:11])=[O:10])[C:5](=[O:8])[NH:6][CH:7]=1.[H-].[Na+].[CH3:15][O:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21]Cl)=[CH:19][CH:18]=1>O>[CH3:15][O:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21][N:6]2[CH:7]=[C:2]([I:1])[C:3]([CH3:12])=[C:4]([N+:9]([O-:11])=[O:10])[C:5]2=[O:8])=[CH:19][CH:18]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 699934-Methyloxybenzyl chlorideHCID 217065145-Iodo-4-methyl-3-nitro-1,2-dihydropyridin-2-one

Produkt 1

HCID 217065161-(4-Methoxybenzyl)-5-iodo-4-methyl-3-nitro-2-pyridoneAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 5-iodo-4-methyl-3-nitro-2-pyridone (2.90 g, 10.4 mmol) and sodium hydride (60% in oil, 0.44 g, 11 mmol) was stirred at rt for 2.5 hours. 4-Methoxybenzyl chloride (1.50 mL) was added, and the mixture was stirred at rt for 18 h. Water was added, and the mixture and extracted with ethyl acetate. The organic phase was washed, dried and evaporated. Chromatography of the residue over silica gel (35% ethyl acetate/petroleum ether) followed by crystallization from water gave 1-(4-methoxybenzyl)-5-iodo-4-methyl-3-nitro-2-pyridone (3.11 g, 75%).

Aufarbeitung

  1. stirringthe mixture was stirred at rt for 18 h
  2. extractionthe mixture and extracted with ethyl acetate
  3. washThe organic phase was washed
  4. customdried
  5. customevaporated
  6. customChromatography of the residue over silica gel (35% ethyl acetate/petroleum ether) followed by crystallization from water

Quellen und Nachweise

ORD-Eintrag
ord-5a5ff7eadff2461cab2adf460f39f474
Quelldatensatz
uspto-grants-2001_09
Patentnummer
US06284768B1

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