Benzyl Chloride → 2-(Benzyloxy)-4,6-dimethylnicotinonitrile

HRID 577453Notes

Reaction equation

HRID 577453 reaction equation
[OH:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([CH3:10])[CH:5]=[C:4]([CH3:11])[N:3]=1.[CH2:12](Cl)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C1(C)C=CC=CC=1>[CH2:12]([O:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([CH3:10])[CH:5]=[C:4]([CH3:11])[N:3]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 7503Benzyl ChlorideHCID 178425241HCID 178425241, compound

Product 1

HCID 229349272-(Benzyloxy)-4,6-dimethylnicotinonitrileYield 65.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 2-hydroxy-4,6-dimethylpyridine-3-carbonitrile (85.0 g, 0.574 mol) and benzyl chloride (87.0 g, 0.688 mol) in toluene (800 mL) was added Ag2O (146 g, 0.631 mol). The reaction mixture was stirred at 110° C. overnight. The reaction mixture was filtered through CELITE® and the solids washed with CH2Cl2. The filtrate was concentrated under vacuum and purified by column chromatography (petroleum ether/EtOAc) to give 2-(benzyloxy)-4,6-dimethylpyridine-3-carbonitrile (Cpd W, 89 g, 65%) as a white solid.

Workup

  1. filtrationThe reaction mixture was filtered through CELITE®
  2. washthe solids washed with CH2Cl2
  3. concentrationThe filtrate was concentrated under vacuum
  4. custompurified by column chromatography (petroleum ether/EtOAc)

Sources & evidence

ORD record
ord-ee3488bec636477baa0d352ba2259ca5
Source dataset
uspto-grants-2015_05
Patent number
US09040515B2

Reaction notes

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