2(1H)-Pyridinone, 1-(2-methoxyphenyl)- → 2-(2-oxo-2H-pyridin-1-yl)-phenol

HRID 379073Notes

Reaction equation

HRID 379073 reaction equation
C(S)C.[Na].[O:5]=[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N:7]1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[O:18]C>CN(C=O)C>[O:5]=[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N:7]1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[OH:18]

Participants

4

Reactant 2

HCID 121913892(1H)-Pyridinone, 1-(2-methoxyphenyl)-HCID 45051917HCID 45051917, compound

Product 1

HCID 216970562-(2-oxo-2H-pyridin-1-yl)-phenol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Sodium ethanethiol (0.108 g, 1.29 mmol) was added to a solution of 2-(2-oxo-2H-pyridin-1-yl)-anisole (0.100 g, 0.497 mmol) in DMF (2 mL), and the reaction mixture was heated at 100° C. for 3 hr. The reaction mixture was partitioned between CHCl3 and saturated aqueous ammonium chloride and treated with 8N HCl (pH=1). The organic layer was separated, washed with H2O, brine, dried (Na2SO4), filtered, concentrated, and taken up in EtOAc, then extracted with 2% NaOH solution. The aqueous basic layer was acidified with 10% HCl solution, then extracted with EtOAc, the organic layer washed with brine, dried (Na2SO4), filtered, and concentrated to give the desired product.

Workup

  1. customThe reaction mixture was partitioned between CHCl3 and saturated aqueous ammonium chloride
  2. additiontreated with 8N HCl (pH=1)
  3. customThe organic layer was separated
  4. washwashed with H2O, brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. extractionextracted with 2% NaOH solution
  9. extractionextracted with EtOAc
  10. washthe organic layer washed with brine
  11. dry with materialdried (Na2SO4)
  12. filtrationfiltered
  13. concentrationconcentrated

Sources & evidence

ORD record
ord-8349e4848ee24d4e9eaa4c73a8acfd17
Source dataset
uspto-grants-2001_10
Patent number
US06297239B1

Reaction notes

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