Sodium ethoxide → 6-Ethoxypyridine-3-carbonitrile
Reaction equation
[O-:1][CH2:2][CH3:3].[Na+].Cl[C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][N:7]=1>C(O)C>[CH2:2]([O:1][C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][N:7]=1)[CH3:3]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Add sodium ethoxide (1.6 mL of 21% w/v in ethanol, 4.8 mmol) to a solution of 6-chloronicotinonitrile (612 mg, 4.41 mmol) in anhydrous ethanol (15 mL) and heat the reaction at reflux for 3 h. Cool to room temperature and stir overnight under nitrogen atmosphere. Concentrate in vacuo and dissolve the residue into dichloromethane. Wash with saturated aqueous NaHCO3, dry over MgSO4 and concentrate in vacuo to give the desired intermediate as an off-white solid (545 mg, 83%).
Workup
- temperatureheat
- customthe reaction
- temperatureat reflux for 3 h
- concentrationConcentrate in vacuo
- dissolutiondissolve the residue into dichloromethane
- washWash with saturated aqueous NaHCO3
- dry with materialdry over MgSO4
- concentrationconcentrate in vacuo
Sources & evidence
- ORD record
- ord-11398d6e6610440b80196300cddb7523
- Source dataset
- uspto-grants-2013_11
- Patent number
- US08580780B2
Reaction notes
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