Sodium ethoxide → 6-Ethoxypyridine-3-carbonitrile

HRID 2041510Notes

Reaction equation

HRID 2041510 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-11398d6e6610440b80196300cddb7523
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

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