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

HRID 1166301Notes

Reaction equation

HRID 1166301 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[Cl:10][C:11]1C=CC(O)=N[CH:16]=1.C([O-])([O-])=O.[K+].[K+].[CH3:24][N:25](C)[C:26](=[O:28])[CH3:27]>C(OCC)(=O)C>[Cl:10][C:11]1[CH:16]=[CH:24][N:25]=[C:26]([O:28][C:2]2[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=2)[CH:27]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 31374DimethylacetamideHCID 680234-FluorobenzaldehydeHCID 1785160645-chloropyridin-2-ol

Product 1

HCID 234332144-[(4-Chloro-2-pyridinyl)oxy]benzaldehydeYield 8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-fluorobenzaldehyde (3.6 g, 29 mmol) in N,N-dimethylacetamide (25 mL) was added 5-chloro-2-pyridinol (4.1 g, 32 mmol) and K2CO3 (4.1 g, 30 mmol) at room temperature under argon. The mixture was heated to reflux for 4 h, cooled to room temperature, diluted with ethyl acetate (150 mL), washed with water and brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by chromatography to yield the title compound as a white solid (0.59 g, 2.5 mmol, 8%). 1H NMR (CDCl3): δ 9.99 (s, 1H), 8.16 (s, 1H), 7.94 (d, J=7.7, 2H), 7.27 (d, J=7.7, 2H), 7.71 (d, J=8.6, 1H), 6.99 (d, J=8.6, 1H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 4 h
  3. washwashed with water and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-9af9926df8bc4f2c90644c9e1ad538a9
Source dataset
uspto-grants-2003_09
Patent number
US06613803B1

Reaction notes

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