Water → 1-Hexyl-5-iodo-4-methyl-3-nitro-2-pyridone

HRID 1387281

Reaktionsgleichung

Reaktionsgleichung von HRID 1387281
[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+].[CH2:15](Br)[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].O>CN(C=O)C>[CH2:15]([N:6]1[CH:7]=[C:2]([I:1])[C:3]([CH3:12])=[C:4]([N+:9]([O-:11])=[O:10])[C:5]1=[O:8])[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Komponenten

6

Edukt 4

HCID 962WaterHCID 81011-BromohexaneHCID 24758Sodium hydrideHCID 217065145-Iodo-4-methyl-3-nitro-1,2-dihydropyridin-2-one

Produkt 1

HCID 217065251-Hexyl-5-iodo-4-methyl-3-nitro-2-pyridone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 5-iodo-4-methyl-3-nitro-2-pyridone (8.0 g, 28.6 mmol) and sodium hydride (1.03 g, 43 mmol) in DMF (150 mL) was stirred at rt for 1 hour. n-Hexyl bromide (8.03 mL, 57.2 mmol) was added, and the mixture was stirred for 24 hours. Water was added, and the mixture was extracted with ethyl acetate. The organic phase was washed, dried, filtered and evaporated. Chromatography of a portion of the residue over silica gel (20% petroleum ether/methylene chloride) gave 1-hexyl-5-iodo-4-methyl-3-nitro-2-pyridone.

Aufarbeitung

  1. stirringthe mixture was stirred for 24 hours
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic phase was washed
  4. customdried
  5. filtrationfiltered
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-823b466d8ffa47918793c6e56a31c61f
Quelldatensatz
uspto-grants-2001_07
Patentnummer
US06268365B1

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