Sodium Bicarbonate → 2-Phenyl-1-pyridin-3-yl-ethanone

HRID 2304597Notes

Reaction equation

HRID 2304597 reaction equation
C([CH:3]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:4]([C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1)=[O:5])#N.C(=O)([O-])O.[Na+]>Br>[C:12]1([CH2:3][C:4]([C:6]2[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=2)=[O:5])[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 3765543beta-Oxo-alpha-phenyl-3-pyridinepropanenitrile

Product 1

HCID 43289002-Phenyl-1-pyridin-3-yl-ethanoneYield 88%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Conditions

Temperature
140 °C

Procedure

2-Cyano-2-phenyl-1-(3-pyridyl)ethanone (5.0 g) was dissolved in 48% hydrobromic acid (50 mL) and the solution was stirred at 140° C. for 5 h. After the mixture was cooled, the mixture was neutralized with an aqueous saturated solution of sodium hydrogen carbonate and the product was extracted with ethyl acetate. The extracts were washed with water, dried, and the solvent was evaporated. The crystalline residue was recrystallized from isopropyl ether to obtain the title compound (3.9 g, yield 88%).

Workup

  1. temperatureAfter the mixture was cooled
  2. extractionthe product was extracted with ethyl acetate
  3. washThe extracts were washed with water
  4. customdried
  5. customthe solvent was evaporated
  6. customThe crystalline residue was recrystallized from isopropyl ether

Sources & evidence

ORD record
ord-45b55f726ce246e39ed5d39f20f85e7d
Source dataset
uspto-grants-2002_08
Patent number
US06436966B1

Reaction notes

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