Pyridine-2-carbonitrile → Methyl Picolinimidate

HRID 1878606Notes

Reaction equation

HRID 1878606 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]#[N:8].[CH3:9][O-:10].[Na+]>CO>[CH3:9][O:10][C:7]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1)=[NH:8]

Participants

4

Reactant 2

HCID 7522Pyridine-2-carbonitrileHCID 10942334Sodium Methoxide

Product 1

HCID 152260Methyl Picolinimidate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Pyridine-2-carbonitrile (Sigma-Aldrich, St. Louis, USA) (1 eq, 190 mmol, 20 g) is dissolved in MeOH (150 ml), then NaOMe (5.4 M in MeOH, 1.1 eq, 209 mmol, 38.7 ml) is added. The resulting mixture is stirred for 16 h at r.t. The solvents are removed in vacuo, then water is added, and the resulting aqueous mixture is extracted with DCM. The organic layer is dried with MgSO4, filtered, and the solvent is removed in vacuo yielding the title compound; [M+H]+=138.

Workup

  1. customThe solvents are removed in vacuo
  2. additionwater is added
  3. extractionthe resulting aqueous mixture is extracted with DCM
  4. dry with materialThe organic layer is dried with MgSO4
  5. filtrationfiltered
  6. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-7aefcdecef4a4346904b266b94d77843
Source dataset
uspto-grants-2012_11
Patent number
US08314112B2

Reaction notes

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