Hydrogen Peroxide → 6-(4-Formylphenoxy)pyridine-3-carboxamide

HRID 228497Notes

Reaction equation

HRID 228497 reaction equation
[CH:1]([C:3]1[CH:17]=[CH:16][C:6]([O:7][C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][N:9]=2)=[CH:5][CH:4]=1)=[O:2].C([O-])([O-])=[O:19].[K+].[K+].OO>CS(C)=O>[CH:1]([C:3]1[CH:17]=[CH:16][C:6]([O:7][C:8]2[CH:15]=[CH:14][C:11]([C:12]([NH2:13])=[O:19])=[CH:10][N:9]=2)=[CH:5][CH:4]=1)=[O:2]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 471502166-(4-Formylphenoxy)nicotinonitrile

Product 1

HCID 568514226-(4-Formylphenoxy)pyridine-3-carboxamideYield 171.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Combine 6-(4-Formyl-phenoxy)-nicotinonitrile (3.02 g, 13.5 mmol), powdered K2CO3 (0.93 g, 6.7 mmol), and DMSO (100 mL) in a RB flask and add H2O2, 30% wt. Aq (4.05 mL, 13.5 mmol) by dropwise addition at 0° C. Stir the reaction mixture for 3 hours allowing it to come to room temperature then quench the reaction slowly at 0° C. with water. Extract the product out of the water layer with ethyl acetate several times and then wash with brine. Dry over Na2SO4 and concentrate under reduced pressure to give 2.78 g (95% yield) of the title compound: 1H NMR (500 MHz, DMSO); 7.2 (1H, d), 7.3-7.4 (2H, m), 7.5 (1H, br s), 7.9-8.0 (2H, m), 8.1 (1H, br s), 8.3 (1H, d), 8.7 (1H, s), 10.0 (1H, s); MS m/z 243 (M+1).

Workup

  1. additionby dropwise addition at 0° C
  2. customto come to room temperature
  3. customthen quench
  4. customthe reaction slowly at 0° C. with water
  5. extractionExtract the product out of the water layer with ethyl acetate several times
  6. washwash with brine
  7. dry with materialDry over Na2SO4
  8. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-e0ef145f8ebd4343ae09e3436a65ed9f
Source dataset
uspto-grants-2009_07
Patent number
US07560463B2

Reaction notes

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