4-Picoline N-oxide → 2-Cyano-4-methylpyridine
Reaction equation
[N+:1]1([O-])[CH:6]=[CH:5][C:4]([CH3:7])=[CH:3][CH:2]=1.C[Si]([C:13]#[N:14])(C)C.N12CCCN=C1CCCCC2>C1COCC1>[C:13]([C:2]1[CH:3]=[C:4]([CH3:7])[CH:5]=[CH:6][N:1]=1)#[N:14]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
To a suspension of 4-picoline N-oxide (13.64 g, 0.124 mole) in 82 ml of THF, under an inert atmosphere, was added trimethylsilyl cyanide (20.1 ml, 0.15 mole) followed by 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) (4.4 ml, 0.028 mole). After stirring at 25 ° C. for 12 hours, the reaction mixture was heated to reflux. After 4.5 hours, the solvent was removed under reduced pressure and the crude sample was eluted with methylene chloride through a pad of Florisil®. The solvent was removed under reduced pressure to provide (8.7 g, 60%) of 2-cyano-4-methyl pyridine, a white crystalline solid: mp 88°-89 ° C. Anal. Calc'd. for C7H6N2 : C, 71.17; H, 5.12; N, 23.71. Found: C, 70.71; H, 5.16; N, 23.44.
Workup
- temperaturethe reaction mixture was heated to reflux
- waitAfter 4.5 hours
- customthe solvent was removed under reduced pressure
- washthe crude sample was eluted with methylene chloride through a pad of Florisil®
- customThe solvent was removed under reduced pressure
Sources & evidence
- ORD record
- ord-918e91be1836408a8f0f1d4926cfa81f
- Source dataset
- uspto-grants-1997_04
- Patent number
- US05616601
Reaction notes
Loading…