Dimethylformamide → HCID 22319077, compound

HRID 547673Notes

Reaction equation

HRID 547673 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-960b48bdf237480b847be8ac6ed8e070
Source dataset
uspto-grants-2011_05
Patent number
US07939549B2

Reaction notes

Loading…