Dimethylformamide → 3-Bromo-1-phenyl-5-(pyridin-2-yl)-1,2-dihydropyridin-2-one

HRID 2356929Notes

Reaction equation

HRID 2356929 reaction equation
[C:1]1([N:7]2[CH:12]=[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=3)[CH:10]=[CH:9][C:8]2=[O:19])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:20]N1C(=O)CCC1=O.CN(C)C=O>BrN1C(=O)CCC1=O.O>[Br:20][C:9]1[C:8](=[O:19])[N:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:12]=[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)[CH:10]=1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 67184N-bromobutanimideHCID 208725951-Phenyl-5-pyridin-2-ylpyridin-2-one

Product 1

HCID 223190653-Bromo-1-phenyl-5-(pyridin-2-yl)-1,2-dihydropyridin-2-oneYield 81%

Reagents, catalysts & solvents 2

HCID 67184N-bromobutanimideCatalystHCID 962WaterSolvent

Conditions

Temperature
4 °C

Procedure

1-Phenyl-5-(pyridin-2-yl)-2(1H)-pyridone (186 g), N-bromosuccinimide (141.7 g) and N,N-dimethylformamide (900 ml) were stirred at room temperature. After 2.5 hr, 6.45 g of N-bromosuccinimide was added thereto. After depletion of the reactant was confirmed, the reaction solution was poured into water (4.5 L) under ice-cooling, followed by stirring in a cold-room (approximately 4° C.) overnight. The resulting crystals were collected by filtration under reduced pressure, followed by dissolving in isopropanol (3.25 L) and water (650 ml) under heating. After the complete dissolution was confirmed, the solution was left to cool gradually, and then ice-cooled. Then, the mixture was stirred in a cold-room overnight. The resulting crystals were collected by filtration under reduced pressure and air-dried at 60° C., to give 191 g (81%) of the title compound.

Workup

  1. temperaturecooling
  2. filtrationThe resulting crystals were collected by filtration under reduced pressure
  3. dissolutionby dissolving in isopropanol (3.25 L)
  4. temperaturewater (650 ml) under heating
  5. dissolutionAfter the complete dissolution
  6. waitthe solution was left
  7. temperatureto cool gradually
  8. temperatureice-cooled
  9. stirringThen, the mixture was stirred in a cold-room overnight
  10. filtrationThe resulting crystals were collected by filtration under reduced pressure
  11. customair-dried at 60° C.

Sources & evidence

ORD record
ord-843bc909eff742d894d2bc89c3769208
Source dataset
uspto-grants-2010_07
Patent number
US07759367B2

Reaction notes

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