Sodium hydride → 1-(2,4-Dimethylbenzyl)-3-methyl-5-nitropyridin-2(1H)-one

HRID 598078

Reaction equation

HRID 598078 reaction equation
[CH3:1][C:2]1[C:3](=[O:11])[NH:4][CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1.[H-].[Na+].Br[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][C:17]=1[CH3:23]>CN(C)C=O>[CH3:23][C:17]1[CH:18]=[C:19]([CH3:22])[CH:20]=[CH:21][C:16]=1[CH2:15][N:4]1[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=[C:2]([CH3:1])[C:3]1=[O:11]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 890973-Methyl-5-nitro-2-pyridoneHCID 27346041-(Bromomethyl)-2,4-dimethylbenzene

Product 1

HCID 672677431-(2,4-Dimethylbenzyl)-3-methyl-5-nitropyridin-2(1H)-oneYield 34%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution containing 0.20 g (1.3 mmol) of 3-methyl-5-nitropyridine-2(1H)-one in 5 ml of N,N-dimethylformamide under a nitrogen atmosphere was added 0.037 g (1.6 mmol) of sodium hydride followed by 0.31 g (1.6 mmol) of 1-bromomethyl-2,4-dimethylbenzene. The reaction was allowed to stir at room temperature for 30 min., quenched with water and extracted with ethyl acetate. The organic phase was dried over magnesium sulfate. Filtration, removal of solvent and purification of the residue via biotage eluting with 25% ethyl acetate/hexanes gave 0.12 g (34%) of compound.

Workup

  1. customquenched with water
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. filtrationFiltration, removal of solvent and purification of the residue via biotage
  5. washeluting with 25% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-5499473fac7046febb2700c5e56811d0
Source dataset
uspto-grants-2011_03
Patent number
US07897607B2

Linked notes

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