Sodium Cyanide → (6-Methoxypyridin-3-yl)acetonitrile

HRID 2176881Notes

Reaction equation

HRID 2176881 reaction equation
[C-:1]#[N:2].[Na+].Cl[CH2:5][C:6]1[CH:7]=[CH:8][C:9]([O:12][CH3:13])=[N:10][CH:11]=1>CS(C)=O.[Cl-].[Na+].O>[CH3:13][O:12][C:9]1[N:10]=[CH:11][C:6]([CH2:5][C:1]#[N:2])=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 137528915-(Chloromethyl)-2-methoxypyridine

Product 1

HCID 45079846(6-Methoxypyridin-3-yl)acetonitrileYield 63.9%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Sodium cyanide (1.25 g, 25.4 mmol) was added to a solution of 5-(chloromethyl)-2-methoxypyridine (1.00 g, 6.34 mmol) in DMSO (10 ml) and stirred for 18 h at room temperature. After completion of reaction, the reaction mixture was diluted with brine and the compound was extracted with DCM (3×35 ml). The combined organic layers were dried over anhydrous sodium sulfate, filtered and evaporated. The crude compound was purified by column chromatography using 100-200 silica gel, 10% ethyl acetate in petroleum ether as eluent to afford 0.6 g (63.8%) of 2-(6-methoxypyridin-3-yl)acetonitrile as white color solid.

Workup

  1. customAfter completion of reaction
  2. extractionthe compound was extracted with DCM (3×35 ml)
  3. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude compound was purified by column chromatography

Sources & evidence

ORD record
ord-cd061ff503fd481db29438cf27ca2bed
Source dataset
uspto-grants-2015_06
Patent number
US09067888B2

Reaction notes

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