Potassium Carbonate → 2(1H)-Pyridinone, 1-(2-methoxyphenyl)-

HRID 379072

Reaction equation

HRID 379072 reaction equation
I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH3:9].[OH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1.C([O-])([O-])=O.[K+].[K+]>[Cu].CCOC(C)=O>[O:10]=[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]1[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH3:9]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 68257o-IodoanisoleHCID 178516071HCID 178516071, compound

Product 1

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

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
200 °C

Procedure

2-Iodoanisole (1.30 mL, 0.01 mol), 2-hydroxypyridine (0.95 g, 0.01 mol), anhydrous K2CO3 (2.76 g, 0.02 mol) and copper powder (0.0636 g, 0.001 mol) were combined and heated at 200° C. for 2 hr. The reaction mixture was cooled, EtOAc added, and filtered. The filtrate was washed with H2O, aqueous saturated NaHCO3 solution, brine, and dried (Na2SO4). Filtration and concentration gave the title compound after chromatography (silica gel, 2% CH3OH, CH2Cl2).

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationfiltered
  3. washThe filtrate was washed with H2O, aqueous saturated NaHCO3 solution, brine
  4. dry with materialdried (Na2SO4)
  5. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-4c3a55ba796041aab00b78a70ae21ba3
Source dataset
uspto-grants-2001_10
Patent number
US06297239B1

Linked notes

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