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

HRID 1594659Notes

Reaction equation

HRID 1594659 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][NH:5][C:4](=[O:8])[C:3]=1[N+:9]([O-:11])=[O:10].[H-].[Na+].[CH3:14][O:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20]Cl)=[CH:18][CH:17]=1.C(OCC)(=O)C>CN(C=O)C>[CH3:14][O:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20][N:5]2[CH:6]=[CH:7][C:2]([CH3:1])=[C:3]([N+:9]([O-:11])=[O:10])[C:4]2=[O:8])=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 699934-Methyloxybenzyl chlorideHCID 3453702-Hydroxy-4-methyl-3-nitropyridine

Product 1

HCID 110111821-(4-Methoxybenzyl)-4-methyl-3-nitro-2-pyridoneYield 56%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred suspension of 4-methyl-3-nitro-2-pyridone (2.0 g, 3 mmol) in DMF (60 mL) was added NaH (60% suspension in oil, 0.52 g). After 1 hour, 4-methoxybenzyl chloride (1.8 mL) was added, and the mixture was stirred at rt overnight. Ethyl acetate was added, and the organic phase was washed with water, dried, filtered and evaporated. Chromatography of the residue over silica gel (ethyl acetate/hexane) gave 1-(4-methoxybenzyl)-4-methyl-3-nitro-2-pyridone (2.0 g, 7.3 mmol, 56%).

Workup

  1. washthe organic phase was washed with water
  2. customdried
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-4a31d0aeb60e4c9aa3d63ad277987e99
Source dataset
uspto-grants-2001_09
Patent number
US06284768B1

Reaction notes

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