Dimethylformamide → 6-(Pyridin-3-yloxy)-pyridine-3-carbaldehyde

HRID 78089

Reaction equation

HRID 78089 reaction equation
[H-].[Na+].CN(C)C=O.[OH:8][C:9]1[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=1.Cl[C:16]1[CH:21]=[CH:20][C:19]([CH:22]=[O:23])=[CH:18][N:17]=1>O>[N:11]1[CH:12]=[CH:13][CH:14]=[C:9]([O:8][C:16]2[N:17]=[CH:18][C:19]([CH:22]=[O:23])=[CH:20][CH:21]=2)[CH:10]=1

Participants

6

Reactant 4

HCID 6228Dimethylformamide3×HCID 79713-HydroxypyridineHCID 24758Sodium hydrideHCID 27640536-Chloropyridine-3-carbaldehyde

Product 1

HCID 592551936-(Pyridin-3-yloxy)-pyridine-3-carbaldehydeYield 36%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of sodium hydride (407 mg, 8.48 mmol, 50% in oil) and N,N-dimethylformamide (45 mL) was added an N,N-dimethylformamide (5 mL) solution of 3-hydroxypyridine (806 mg, 8.48 mmol) at 0° C., which was stirred for 30 minutes. An N,N-dimethylformamide (5 mL) solution of 2-chloro-5-formylpyridine (1.0 g, 7.06 mmol) was added to this reaction mixture at the same temperature, which was stirred for 5 hours at 100° C. The reaction mixture was cooled to room temperature, and water was added thereto, which was extracted with ethyl acetate. The organic layer was separated, washed with water and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure, and the residue was purified by NH silica gel column chromatography (ethyl acetate) to obtain the title compound (505.1 mg, 36%).

Workup

  1. stirringwas stirred for 5 hours at 100° C
  2. extractionwhich was extracted with ethyl acetate
  3. customThe organic layer was separated
  4. washwashed with water and saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under a reduced pressure
  8. customthe residue was purified by NH silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-a48fa208865b4d5b8702eea204cd5d0f
Source dataset
uspto-grants-2014_09
Patent number
US08841327B2

Linked notes

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