HCID 18182237, compound → (2-Methoxypyridin-4-yl)(phenyl)methanone

HRID 1359257Notes

Reaction equation

HRID 1359257 reaction equation
[CH3:1][OH:2].C[O-].[Na+].[C:6]([C:14]1[CH:19]=[CH:18][N:17]=[C:16](Cl)[CH:15]=1)(=[O:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>CO>[C:6]([C:14]1[CH:19]=[CH:18][N:17]=[C:16]([O:2][CH3:1])[CH:15]=1)(=[O:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 18182237HCID 18182237, compoundHCID 23694274Sodium methanolate methanol

Product 1

HCID 2762474(2-Methoxypyridin-4-yl)(phenyl)methanone

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

While heating under reflux a 28% sodium methoxide methanol solution mildly, a mixture of 135 g of 4-benzoyl-2-chloropyridine and 150 ml of methanol was added dropwise thereinto over one hour, followed by heating under reflux for further 2 hours. After cooling as it was, the reaction solution was filtered to remove insoluble matters and the solvent was removed. To the residue was added an aqueous sodium bicarbonate solution and the mixture was extracted with ethyl acetate. The organic phase was washed with brine, dried over anhydrous magnesium sulfate and then the solvent was removed, to give 130 g of the target compound.

Workup

  1. temperatureWhile heating
  2. additionwas added dropwise
  3. temperatureby heating
  4. temperatureunder reflux for further 2 hours
  5. temperatureAfter cooling as it
  6. filtrationthe reaction solution was filtered
  7. customto remove insoluble matters
  8. customthe solvent was removed
  9. additionTo the residue was added an aqueous sodium bicarbonate solution
  10. extractionthe mixture was extracted with ethyl acetate
  11. washThe organic phase was washed with brine
  12. dry with materialdried over anhydrous magnesium sulfate
  13. customthe solvent was removed

Sources & evidence

ORD record
ord-41e83d81981d4702b607175fa341d6a7
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Reaction notes

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