Dimethylformamide → HCID 22319077, compound

HRID 497804Notes

Reaction equation

HRID 497804 reaction equation
CN(C)C=O.[N:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]1=[O:18].[Br:19]N1C(=O)CCC1=O>O>[N:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N:12]1[CH:17]=[C:16]([Br:19])[CH:15]=[CH:14][C:13]1=[O:18]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 67184N-bromobutanimideHCID 598976[1(2H),2'-Bipyridin]-2-one

Product 1

HCID 22319077HCID 22319077, compoundYield 51.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under ice-cooling, 15 ml of a dimethylformamide solution containing 1.50 g of 1-(2-pyridyl)-1,2-dihydropyridin-2-one was incorporated with 1.60 g of N-bromosuccinic acid imide. The mixture was stirred at room temperature for 2 hours, and then diluted with water and extracted with ethyl acetate. The organic layer was washed with water and brine, and then dried over magnesium sulfate. The solvent was evaporated, and the residue was purified by silica gel chromatography (ethyl acetate/hexane=1:3), to give 1.13 g of the title compound as a pale brown powder.

Workup

  1. temperatureUnder ice-cooling
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated
  6. customthe residue was purified by silica gel chromatography (ethyl acetate/hexane=1:3)

Sources & evidence

ORD record
ord-fdc8b7b53f9c4da18423face1e132e3d
Source dataset
uspto-grants-2005_09
Patent number
US06949571B2

Reaction notes

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