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

HRID 577463Notes

Reaction equation

HRID 577463 reaction equation
[OH:1][C:2]1[N:9]=[C:8]([CH3:10])[CH:7]=[C:6]([CH3:11])[C:3]=1[C:4]#[N:5].[CH2:12](Cl)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>[Ag-]=O.C1(C)C=CC=CC=1>[CH2:12]([O:1][C:2]1[N:9]=[C:8]([CH3:10])[CH:7]=[C:6]([CH3:11])[C:3]=1[C:4]#[N:5])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 2

HCID 7503Benzyl ChlorideHCID 178425241HCID 178425241, compound

Product 1

HCID 229349272-(Benzyloxy)-4,6-dimethylnicotinonitrileYield 94.4%

Reagents, catalysts & solvents 2

HCID 178418778HCID 178418778, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 2-hydroxy-4,6-dimethylnicotinonitrile (5.3 g, 36 mmol), benzyl chloride (5.7 mL, 45 mmol), silver(I)oxide (9.2 g, 40 mmol) and toluene (50 mL) were heated at 110° C. in a sealed tube for 20 hours. The mixture was cooled to room temperature and the solids were filtered and rinsed with dichloromethane. The filtrate was concentrated under vacuum and purified by column chromatography (40% EtOAc/Heptane) to give 2-(benzyloxy)-4,6-dimethylnicotinonitrile (Cpd II, 8.1 g, 94% yield) as a white solid.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationthe solids were filtered
  3. washrinsed with dichloromethane
  4. concentrationThe filtrate was concentrated under vacuum
  5. custompurified by column chromatography (40% EtOAc/Heptane)

Sources & evidence

ORD record
ord-fbdea4f4fbf44429b994552a19fab072
Source dataset
uspto-grants-2015_05
Patent number
US09040515B2

Reaction notes

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