Ethanol → 3-Ethoxyisonicotinonitrile
Reaction equation
[Na].Cl[C:3]1[CH:4]=[N:5][CH:6]=[CH:7][C:8]=1[C:9]#[N:10].[CH2:11]([OH:13])[CH3:12]>>[CH2:11]([O:13][C:3]1[CH:4]=[N:5][CH:6]=[CH:7][C:8]=1[C:9]#[N:10])[CH3:12]Participants
4
Procedure
A mixture of sodium metal (1.4 g, 0.06 mol) and ethanol (10 ml) was stirred until all of the sodium metal had dissolved and the solvent was removed in vacuo. The residue was placed under argon, and DMF (50 ml), followed by 3-chloro-4-cyanopyridine (6.95 g, 0.05 mol) were added at 5° C. The mixture was warmed to room temperature and stirred for 24 hours. The solvent was removed in vacuo and the residue was treated with dichloromethane and filtered. The filtrate was removed in vacuo, the residue was treated with water and a solid was collected by filtration to afford 4.6 g (62%) of 3-ethoxy-4-cyanopyridine as a tan solid, m.p. 56°-57° C.
Workup
- dissolutionhad dissolved
- customthe solvent was removed in vacuo
- additionwere added at 5° C
- customThe solvent was removed in vacuo
- additionthe residue was treated with dichloromethane
- filtrationfiltered
- customThe filtrate was removed in vacuo
- additionthe residue was treated with water
- filtrationa solid was collected by filtration
Sources & evidence
- ORD record
- ord-e9839332963b4e329ab69030bb5001ab
- Source dataset
- uspto-grants-1994_03
- Patent number
- US05294612
Reaction notes
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