Potassium Carbonate → Methyl [(2-cyanopyridin-3-yl)oxy]acetate

HRID 2109058Notes

Reaction equation

HRID 2109058 reaction equation
[C:1]([C:3]1[C:8]([OH:9])=[CH:7][CH:6]=[CH:5][N:4]=1)#[N:2].Br[CH2:11][C:12]([O:14][CH3:15])=[O:13].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[C:1]([C:3]1[C:8]([O:9][CH2:11][C:12]([O:14][CH3:15])=[O:13])=[CH:7][CH:6]=[CH:5][N:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 1019203-Hydroxypyridine-2-carbonitrile

Product 1

HCID 57633316Methyl [(2-cyanopyridin-3-yl)oxy]acetateYield 98.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2-Cyano-3-hydroxypyridine (5.00 g) is dissolved in acetone (50 ml), and thereto are added methyl bromoacetate (7.0 g) and potassium carbonate (6.3 g). The mixture is heated under reflux for 1.5 hours. After allowing to cool, ice-water is poured to the reaction solution and extracted with ethyl acetate. The organic layer is washed with saturated brine, dried over sodium sulfate and evaporated to remove the solvent under reduced pressure. The resulting residue is suspended in diethyl ether/n-hexane and the solid is collected by filtration to give the title compound (7.91 g).

Workup

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for 1.5 hours
  3. temperatureto cool
  4. extractionextracted with ethyl acetate
  5. washThe organic layer is washed with saturated brine
  6. dry with materialdried over sodium sulfate
  7. customevaporated
  8. customto remove the solvent under reduced pressure
  9. filtrationthe solid is collected by filtration

Sources & evidence

ORD record
ord-626e3a24cef343b0b01c208e09b1afa6
Source dataset
uspto-grants-2009_04
Patent number
US07514449B2

Reaction notes

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