4-Chloro-nicotinonitrile → 4-Methoxynicotinonitrile

HRID 1830859Notes

Reaction equation

HRID 1830859 reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[CH:4][CH:3]=1.[CH3:10][O-:11].[Na+].CO>CO>[CH3:10][O:11][C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 134111124-Chloro-nicotinonitrileHCID 23694274Sodium methanolate methanol

Product 1

HCID 27558874-MethoxynicotinonitrileYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of compound (20)(2.77 g, 20.0 mmol) in methanol (5 ml) was added a 28% sodium methylate-methanol solution (5.0 g, 24.0 mmol) at room temperature and the mixture was stirred for one hr. The solvent was concentrated and the obtained residue was partitioned between ethyl acetate and iced-brine. The organic layer was dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. The obtained residue was recrystallized from a small amount of isopropyl ether to give the title compound (2.3 g, 86%).

Workup

  1. concentrationThe solvent was concentrated
  2. customthe obtained residue was partitioned between ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was recrystallized from a small amount of isopropyl ether

Sources & evidence

ORD record
ord-0455b632e971400ca5ad7073ae0221fb
Source dataset
uspto-grants-2006_06
Patent number
US07067537B2

Reaction notes

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