Potassium Carbonate → 1-(3-Furanyl)-4-methyl-2(1H)-pyridinone

HRID 2236886Notes

Reaction equation

HRID 2236886 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][N:3]=1.Br[C:10]1[CH:14]=[CH:13][O:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.[OH-].[NH4+].[Cu]I>[O:12]1[CH:13]=[CH:14][C:10]([N:3]2[CH:4]=[CH:5][C:6]([CH3:8])=[CH:7][C:2]2=[O:1])=[CH:11]1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 891643-BromofuranHCID 178428601HCID 178428601, compound

Product 1

HCID 426257441-(3-Furanyl)-4-methyl-2(1H)-pyridinoneYield 62%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolventHCID 14923Ammonium HydroxideSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of 2-hydroxy-4-methylpyridine (0.66 g, 6.0 mmol), 3-bromofuran (1.7 g, 12 mmol), copper (I) iodide (0.11 g, 0.60 mmol), and potassium carbonate (0.84 g, 6.0 mmol) in N,N-dimethylformamide (12 mL) were heated at 180° C. for 2 hours in a 300 W microwave reactor. The completed reaction mixture is diluted with 10% aqueous ammonium hydroxide solution and extracted 3× with ethyl acetate. The combined extracts were washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give 1-furan-3-yl-4-methyl-1H-pyridin-2-one (0.65 g, 62%).

Workup

  1. customThe completed reaction mixture
  2. extractionextracted 3× with ethyl acetate
  3. washThe combined extracts were washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-51cffdd047504f8388a7dd64227ac683
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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