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

HRID 1005403

Reaction equation

HRID 1005403 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-3f4e5e9441024e23af003f648c90ef2f
Source dataset
uspto-grants-2000_04
Patent number
US06054470

Linked notes

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