Methanol → 2-Methoxy-4,6-dimethylnicotinonitrile

HRID 577450Notes

Reaction equation

HRID 577450 reaction equation
[Na].Cl[C:3]1[C:8]([C:9]#[N:10])=[C:7]([CH3:11])[CH:6]=[C:5]([CH3:12])[N:4]=1.[CH3:13][OH:14]>>[CH3:13][O:14][C:3]1[C:8]([C:9]#[N:10])=[C:7]([CH3:11])[CH:6]=[C:5]([CH3:12])[N:4]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 2232612-Chloro-4,6-dimethyl-3-pyridinecarbonitrileHCID 5360545Sodium2×

Product 1

HCID 5952762-Methoxy-4,6-dimethylnicotinonitrileYield 100%

Conditions

Temperature
70 °C

Procedure

Sodium (23 g, 0.99 mol) was added to dry MeOH (800 mL) portion-wise. After the addition, the mixture was stirred for an hour until the sodium was mostly dissolved. To the reaction mixture was added 2-chloro-4,6-dimethylpyridine-3-carbonitrile (110 g, 0.66 mol). The resulting mixture was heated at 70° C. and stirred for four hours. The suspension was filtered and the filtrate was concentrated under vacuum. The residue was purified by column chromatography (petroleum ether/EtOAc, 10:1) to give 2-methoxy-4,6-dimethylpyridine-3-carbonitrile (Cpd S, 103 g, 100%) as a white solid.

Workup

  1. additionAfter the addition
  2. dissolutionwas mostly dissolved
  3. filtrationThe suspension was filtered
  4. concentrationthe filtrate was concentrated under vacuum
  5. customThe residue was purified by column chromatography (petroleum ether/EtOAc, 10:1)

Sources & evidence

ORD record
ord-32199505d69e4a5f86474ea237768681
Source dataset
uspto-grants-2015_05
Patent number
US09040515B2

Reaction notes

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