Ethyl Acetate → 1-(4-Methoxybenzyl)-5-bromo-4-methyl-3-nitro-2-pyridone

HRID 1387273

Reaction equation

HRID 1387273 reaction equation
[Br: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.C(OCC)(=O)C>CN(C=O)C>[CH3:15][O:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21][N:6]2[CH:7]=[C:2]([Br:1])[C:3]([CH3:12])=[C:4]([N+:9]([O-:11])=[O:10])[C:5]2=[O:8])=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 699934-Methyloxybenzyl chlorideHCID 217065175-Bromo-2-hydroxy-4-methyl-3-nitropyridine

Product 1

HCID 217064791-(4-Methoxybenzyl)-5-bromo-4-methyl-3-nitro-2-pyridoneYield 68%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 5-bromo-4-methyl-3-nitro-2-pyridone (0.60 g, 2.5 mmol) in DMF (15 mL) was added sodium hydride (60% suspension in oil, 0.103 g). After 30 minutes, 4-methoxybenzyl chloride (0.35 mL) was added, and the mixture was stirred overnight at rt. Ethyl acetate was added and the organic phase was washed with water, dried (Na2SO4), filtered and evaporated. Chromatography of the residue over silica gel (ethyl acetate/hexane 1/1)) gave 1-(4-methoxybenzyl)-5-bromo-4-methyl-3-nitro-2-pyridone (0.60 g, 1.7 mmol, 68%).

Workup

  1. washthe organic phase was washed with water
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-a2fc566f34854035be24dc6d451663a6
Source dataset
uspto-grants-2001_07
Patent number
US06268365B1

Linked notes

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