Acetic Acid → Methyl Picolinimidate
Reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1)#[N:2].C[O-].[Na+].[C:12](O)(=[O:14])C>CO>[N:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[C:1](=[NH:2])[O:14][CH3:12]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
2-cyanopyridine (10.0 g, 96.1 mmol) was dissolved in methanol (50 ml). Sodium methoxide (0.26 g, 4.8 mmol) was added to the solution, and reaction was conducted for 6 hours at room temperature. After the reaction was completed, acetic acid (0.32 g, 5.3 mmol) was added to neutralize the reaction solution, and the solution was concentrated under reduced pressure. Diethyl ether (50 ml) was added to the concentrated residue, and diethyl ether insoluble products were removed by filtration. The filtrate was concentrated under reduced pressure to give the crude product of methyl 2-pyridinecarboximidate as a pale yellow oil in a yield of 7.5 g.
Workup
- concentrationthe solution was concentrated under reduced pressure
- additionDiethyl ether (50 ml) was added to the concentrated residue, and diethyl ether insoluble products
- customwere removed by filtration
- concentrationThe filtrate was concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-0d3bb46abd0b49c190ba7150301d1cec
- Source dataset
- uspto-grants-1992_11
- Patent number
- US05166347
Reaction notes
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