Potassium Carbonate → 4-[(6-Methyl-2-pyridinyl)oxy]benzaldehyde

HRID 705909Notes

Reaction equation

HRID 705909 reaction equation
[CH3:1][C:2]1[NH:7][C:6](=[O:8])[CH:5]=[CH:4][CH:3]=1.F[C:10]1[CH:17]=[CH:16][C:13]([CH:14]=[O:15])=[CH:12][CH:11]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[CH3:1][C:2]1[N:7]=[C:6]([O:8][C:10]2[CH:17]=[CH:16][C:13]([CH:14]=[O:15])=[CH:12][CH:11]=2)[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 680234-FluorobenzaldehydeHCID 767726-Methylpyridin-2-ol

Product 1

HCID 866662114-[(6-Methyl-2-pyridinyl)oxy]benzaldehydeYield 83%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

To a solution of 6-methyl-2(1H)-pyridinone (2 g, 18.33 mmol) and 4-fluorobenzaldehyde (2 ml, 18.64 mmol) in DMF (60 mL), was added K2CO3 (3.80 g, 27.5 mmol). The mixture was heated at 130° C. overnight. After cooling, the reaction mixture was diluted in water, extracted with EA. The organic phase was washed with water and brine, dried over Na2SO4, concentrated to afford the title compound (3.24 g, 15.19 mmol, 83% yield) as a brown oil. LCMS: rt=2.77 min, [M+H+]=214

Workup

  1. temperatureAfter cooling
  2. extractionextracted with EA
  3. washThe organic phase was washed with water and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b63e80106eb54fad9983235895cf5c9e
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

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