Sodium Methoxide → 5-Methoxypyridine-2-carbonitrile

HRID 431851Notes

Reaction equation

HRID 431851 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6](F)=[CH:5][N:4]=1)#[N:2].[CH3:10][O-:11].[Na+]>C(OCC)(=O)C>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([O:11][CH3:10])=[CH:5][N:4]=1)#[N:2]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 113324532-Cyano-5-fluoropyridine

Product 1

HCID 131442795-Methoxypyridine-2-carbonitrileYield 43%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-cyano-5-fluoropyridine (0.65 g, 5.3 mmol) in sodium methoxide (1.83 mL of 25% wt. solution in methanol, 7.95 mmol) was stirred at 0° C. for 1.5 hours and 2 hours at ambient temperature. The reaction was then diluted with ethyl acetate and washed with water and brine. Removal of the solvent in vacuo afforded 304 mg (43%) of 2-cyano-5-methoxypyridine.

Workup

  1. washwashed with water and brine
  2. customRemoval of the solvent in vacuo

Sources & evidence

ORD record
ord-a3af1b2bb05d46d0ad0aad956a6d552a
Source dataset
uspto-grants-2003_12
Patent number
US06660753B2

Reaction notes

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