Hydrogen Peroxide → 3-(Cyanomethyl)pyridin-1-ium-1-olate
Reaction equation
[OH:1]O.[N:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][C:10]#[N:11])[CH:4]=1.O>C(O)(=O)C>[CH:7]1[CH:8]=[N+:3]([O-:1])[CH:4]=[C:5]([CH2:9][C:10]#[N:11])[CH:6]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 95 °C
Procedure
30% Hydrogen peroxide (12 mL) was added to a solution of 3-pyridylacetonitrile (7.50 g, 63.5 mmol) in acetic acid (40 mL) and the mixture heated at 95° C. for 20 hours. The reaction mixture was then cooled and stirred at room temperature for 72 hours. Water (35 mL) was then added and the solution concentrated under reduced pressure. Water (2×100 mL) was added to the residue and solution concentrated under reduced pressure. Residual water was removed azeotropically using toluene (2×100 mL) to yield the title compound (I115) (8.3 g, 97%) as a pale yellow solid which was used without further purification.
Workup
- temperatureThe reaction mixture was then cooled
- concentrationthe solution concentrated under reduced pressure
- additionWater (2×100 mL) was added to the residue and solution
- concentrationconcentrated under reduced pressure
- customResidual water was removed azeotropically using toluene (2×100 mL)
Sources & evidence
- ORD record
- ord-c2a848c6d4d844269bb9f791cb9cf1a7
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09421205B2
Reaction notes
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