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

HRID 1387281Notes

Reaction equation

HRID 1387281 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-823b466d8ffa47918793c6e56a31c61f
Source dataset
uspto-grants-2001_07
Patent number
US06268365B1

Reaction notes

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