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

HRID 2167194Notes

Reaction equation

HRID 2167194 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:8]=[CH:9][C:10](=[O:19])[N:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:12]=1.[Br:20]N1C(=O)CCC1=O.CN(C)C=O.CC(O)C>O>[Br:20][C:9]1[C:10](=[O:19])[N:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:12]=[C:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)[CH:8]=1

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 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 86.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
30 °C

Procedure

5-(2-Pyridyl)-1-phenyl-1,2-dihydropyridine-2-one (300 g), N-bromosuccinimide (236.5 g) and N,N-dimethylformamide (1.8 L) were placed in a 10-L reactor, and the reaction mixture was stirred at 30° C. (external temperature) in a nitrogen stream for 3 hours and 15 minutes. 2-Propanol (4.2 L) was added dropwise to the reaction mixture over a period of 9 minutes, followed by adding thereto water (2.1 L) over a period of 7 minutes. The resulting mixture was heated at 85° C. (external temperature) with stifling. After confirming the dissolution of the contents, the resulting solution was stirred at an external temperature of 55° C. for 1 hour. Thereafter, the solution was stirred at 40° C. (external temperature) for another 22 minutes, at 30° C. (external temperature) for further another 23 minutes, and then at 10° C. (external temperature) for still another 15 hours and 15 minutes. The reaction mixture was filtered and the precipitate was washed with 50% 2-propanol-water (2.4 L) and then dried under reduced pressure (60° C., 6 hours) to obtain 341.45 g of 3-bromo-5-(2-pyridyl)-1-phenyl-1,2-dihydropyridine-2-one. Yield: 86.4%. 1H NMR (400 MHz, CDCl3) δ 8.59-8.56 (m, 1H), 8.50 (d, 1H), 8.18 (d, 1H), 7.72 (td, 1H), 7.53-7.41 (m, 6H), 7.20 (ddd, 1H).

Workup

  1. custom15 minutes
  2. additionby adding
  3. temperatureThe resulting mixture was heated at 85° C. (external temperature)
  4. dissolutionthe dissolution of the contents
  5. stirringthe resulting solution was stirred at an external temperature of 55° C. for 1 hour
  6. stirringThereafter, the solution was stirred at 40° C. (external temperature) for another 22 minutes
  7. waitat 30° C. (external temperature) for further another 23 minutes
  8. waitat 10° C. (external temperature) for still another 15 hours
  9. custom15 minutes
  10. filtrationThe reaction mixture was filtered
  11. washthe precipitate was washed with 50% 2-propanol-water (2.4 L)
  12. customdried under reduced pressure (60° C., 6 hours)

Sources & evidence

ORD record
ord-d3caf24c3cdd4d77a02d7d3ebc0717c9
Source dataset
uspto-grants-2015_06
Patent number
US09045426B2

Reaction notes

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