Water → 2-(benzyloxy)isonicotinonitrile

HRID 748133Notes

Reaction equation

HRID 748133 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]#[N:9])[CH:5]=[CH:4][N:3]=1.C([O:13][CH2:14][CH3:15])(=O)C.O>O1CCCC1>[CH2:14]([O:13][C:2]1[CH:7]=[C:6]([CH:5]=[CH:4][N:3]=1)[C:8]#[N:9])[C:15]1[CH:2]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 8857Ethyl AcetateHCID 5686382-Chloro-4-cyanopyridine

Product 1

HCID 225035202-(benzyloxy)isonicotinonitrileYield 62%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-chloro-4-cyanopyridine (0.40 g, 2.9 mmol) in tetrahydrofuran (1 ml) was added to the mixture and the mixture was refluxed for 6 hrs. The reaction mixture was combined with ethyl acetate and water and stirred. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated. The residue was subjected to a silica gel (30 g) column chromatography, eluted with hexane-ethyl acetate (4:1, v/v) to give the titled compound (0.37 g, 62%).

Workup

  1. temperaturethe mixture was refluxed for 6 hrs
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated
  5. washeluted with hexane-ethyl acetate (4:1

Sources & evidence

ORD record
ord-b2c68642cc40489699b0144a9a3bd3b4
Source dataset
uspto-grants-2008_07
Patent number
US07399759B2

Reaction notes

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