Dimethylformamide → 1-(4-METHOXYPHENYL)PYRIDIN-2(1H)-ONE

HRID 1693079Notes

Reaction equation

HRID 1693079 reaction equation
[C:1](=[O:4])([O-])[O-].[K+].[K+].CN(C)C=O.O[C:13]1[CH:18]=C[N:16]=[CH:15][CH:14]=1.I[C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1>[Cu](I)I.O>[CH3:27][O:26][C:23]1[CH:24]=[CH:25][C:20]([N:16]2[CH:15]=[CH:14][CH:13]=[CH:18][C:1]2=[O:4])=[CH:21][CH:22]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 696764-IodoanisoleHCID 178418642HCID 178418642, compound

Product 1

HCID 121913851-(4-METHOXYPHENYL)PYRIDIN-2(1H)-ONEYield 51.4%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

Potassium carbonate (1.16 g, 8.41 mmol) and copper iodide (16 mg, 0.084 mmol) were added to a dimethylformamide (12 mL) solution of 4-hydroxypyridine (800 mg, 8.41 mmol) and 4-iodo-1-methoxybenzene (3.94 g, 16.8 mmol), and stirred at 150° C. for 21 hours. The reaction mixture was cooled to room temperature, then water was added to the reaction mixture, and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried with anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was purified through silica gel column chromatography (C-300, hexane/ethyl acetate=1/1) to obtain the entitled compound (870 mg, 51%).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried with anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified through silica gel column chromatography (C-300, hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-369dc2aa1d444e1799749a86758b7447
Source dataset
uspto-grants-2012_04
Patent number
US08158652B2

Reaction notes

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