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

HRID 497877Notes

Reaction equation

HRID 497877 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>C1C(=O)N(Br)C(=O)C1.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 NBS 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 IPA (3.25 L) and H2O (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 IPA (3.25 L)
  4. temperatureH2O (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-adccf9ba9bb8490f83e4468bc600b4d9
Source dataset
uspto-grants-2005_09
Patent number
US06949571B2

Reaction notes

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