N-bromobutanimide → 3-Bromo-1-methyl-5-nitro-2(1H)-pyridinone

HRID 598052Notes

Reaction equation

HRID 598052 reaction equation
[CH3:1][N:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]1=[O:11].[Br:12]N1C(=O)CCC1=O>CN(C)C=O.ClCCl>[Br:12][C:4]1[C:3](=[O:11])[N:2]([CH3:1])[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 2958661-methyl-5-nitro-2(1H)-pyridinone

Product 1

HCID 672674813-Bromo-1-methyl-5-nitro-2(1H)-pyridinoneYield 72.15%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution containing 0.55 g (3.57 mmol) of 1-methyl-5-nitropyridin-2(1H)-one in 10 ml of N,N-dimethylformamide under a nitrogen atm. was added 0.76 g (4.27 mmol) of N-bromosuccinimide. The reaction was allowed to stir at 25° C. overnight. The reaction was diluted with dichloromethane and washed with water. The organic phase was dried over magnesium sulfate. Filtration, removal of solvent and purification of the residue via biotage eluting with 70% ethyl acetate/hexanes gave 0.60 g (72.15%) of product as a white solid.

Workup

  1. washwashed with water
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. filtrationFiltration, removal of solvent and purification of the residue via biotage
  4. washeluting with 70% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-57a353319efd4a0f9f44814c4bb2984f
Source dataset
uspto-grants-2011_03
Patent number
US07897607B2

Reaction notes

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