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

HRID 1387279

Reaction equation

HRID 1387279 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 l s 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. extractionextracted 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-19ee25c0c6844f1da92b3f602ab6c41b
Source dataset
uspto-grants-2001_07
Patent number
US06268365B1

Linked notes

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