2-Chloro-4,6-dimethyl-3-pyridinecarbonitrile → 2-Methoxy-4,6-dimethylnicotinonitrile

HRID 1921333Notes

Reaction equation

HRID 1921333 reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[C:6]([CH3:10])[CH:5]=[C:4]([CH3:11])[N:3]=1.[CH3:12][O-:13].[Na+]>CO.O>[C:8]([C:7]1[C:2]([O:13][CH3:12])=[N:3][C:4]([CH3:11])=[CH:5][C:6]=1[CH3:10])#[N:9]

Participants

5

Reactant 2

HCID 2232612-Chloro-4,6-dimethyl-3-pyridinecarbonitrileHCID 10942334Sodium Methoxide

Product 1

HCID 5952762-Methoxy-4,6-dimethylnicotinonitrileYield 65%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 2-chloro-3-cyano-4,6-dimethylpyridine (4.60 g, 27.7 mmol) in methanol (30 mL) is added to a stirred solution of sodium methoxide (2.09 g, 38.78 mmol) in methanol (20 mL) and the reaction mixture is heated at 60° C. for 4 hr. After cooling, the reaction is diluted with water (150 mL) and the solids are collected by filtration, washed with water and dried to yield 3-cyano-4,6-dimethyl-2-methoxypyridine (2.90 g, 65%) as an off-white solid containing the same impurity as the starting material. LC/MS: MS m/e=163 (M+H); RT 3.29 min; 1H NMR (CDCl3, δ ppm) 6.69, (1H, s), 4.00 (3H, s), 2.43 (6H, s).

Workup

  1. temperatureAfter cooling
  2. filtrationthe solids are collected by filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-8935945725ef43069bc3c780b2f3570b
Source dataset
uspto-grants-2012_05
Patent number
US08173682B2

Reaction notes

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