Sodium ethoxide → 6-Ethoxypyridine-3-carbonitrile

HRID 911646Notes

Reaction equation

HRID 911646 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

HCID 2723922Sodium ethoxideHCID 51520946-Chloro-3-pyridinecarbonitrile

Product 1

HCID 189294456-Ethoxypyridine-3-carbonitrileYield 83.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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

  1. temperatureheat
  2. customthe reaction
  3. temperatureat reflux for 3 h
  4. concentrationConcentrate in vacuo
  5. dissolutiondissolve the residue into dichloromethane
  6. washWash with saturated aqueous NaHCO3
  7. dry with materialdry over MgSO4
  8. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-9b0eae05722041a3af587a341eadbbe7
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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