3-Cyanopyridine → 3-Pyridinecarboximidic acid, methyl ester

HRID 1952748Notes

Reaction equation

HRID 1952748 reaction equation
[C:1](#[N:8])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.C[O-].[Na+].[C:12](O)(=[O:14])C>CO>[N:4]1[CH:5]=[CH:6][CH:7]=[C:2]([C:1](=[NH:8])[O:14][CH3:12])[CH:3]=1

Participants

5

Reactant 3

HCID 793-CyanopyridineHCID 176Acetic AcidHCID 10942334Sodium Methoxide

Product 1

HCID 103293433-Pyridinecarboximidic acid, methyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of nicotinonitrile (11.35 g) and sodium methoxide (1.1 g) in methanol was allowed to stand at ambient temperature under nitrogen for 18 hours, then acetic acid (1.2 ml) was added, and the solvent was removed in vacuo. The residue was triturated with cyclohexane, undissolved solid was removed by filtration, and the solvent was removed in vacuo to leave methyl pyridine-3-carboximidate as an orange oil (10.6 g).

Workup

  1. customthe solvent was removed in vacuo
  2. customThe residue was triturated with cyclohexane, undissolved solid
  3. customwas removed by filtration
  4. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-4c206c5bd049428ca5840ce598c209d9
Source dataset
uspto-grants-2000_09
Patent number
US06114334

Reaction notes

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