Dimethylformamide → 6-Chloropyridine-2-carbonitrile
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4](S(C)(=O)=O)[N:3]=1.[C-]#N.[Na+].[CH3:15][N:16](C=O)C>O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:15]#[N:16])[N:3]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 170 °C
Procedure
A mixture of 2-chloro-6-methylsulfonylpyridine (13.0 g, 67.8 mmol), sodium cyanide (6.69 g, 136 mmol) and DMF (150 ml) was stirred at 170° C. for 18 hrs. After cooling, the reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with saturated brine and dried, and the solvent was evaporated under reduced pressure. The residue was subjected to a silica gel column chromatography and eluted with hexane-ethyl acetate (2:1, v/v) to give 2-chloro-6-cyanopyridine (6.67 g, 71%) as crystals (mp. 82.9-83.1° C.).
Workup
- temperatureAfter cooling
- extractionextracted with ethyl acetate
- washThe extract was washed with saturated brine
- customdried
- customthe solvent was evaporated under reduced pressure
- washeluted with hexane-ethyl acetate (2:1
Sources & evidence
- ORD record
- ord-69ed0cbeb2e74332aee109c312fe892c
- Source dataset
- uspto-grants-2010_08
- Patent number
- US07767665B2
Reaction notes
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