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

HRID 1594668Notes

Reaction equation

HRID 1594668 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+].[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-5a5ff7eadff2461cab2adf460f39f474
Source dataset
uspto-grants-2001_09
Patent number
US06284768B1

Reaction notes

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