Benzyl Alcohol → 2-(Benzyloxy)nicotinonitrile

HRID 1294208Notes

Reaction equation

HRID 1294208 reaction equation
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:10]1[C:15]([C:16]#[N:17])=[CH:14][CH:13]=[CH:12][N:11]=1.CN(C)C=O.[H-].[Na+]>O>[CH2:1]([O:8][C:10]1[N:11]=[CH:12][CH:13]=[CH:14][C:15]=1[C:16]#[N:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 810792-Chloronicotinonitrile

Product 1

HCID 126045112-(Benzyloxy)nicotinonitrileYield 69.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of benzyl alcohol (32.0 g), 2-chloro-3-cyanopyridine (37.3 g) and N,N-dimethylformamide (200 mL) was added sodium hydride (60%, oil, 12.92 g) under ice-cooling. The reaction mixture was stirred at room temperature for 3 days. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated. The obtained residue was subjected to silica gel column chromatography to give 2-(benzyloxy)nicotinonitrile as an oil (39.13 g, 69%) from a fraction eluted with ethyl acetate-hexane (1:6, v/v).

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed successively with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1a94fac5397c442e8df7d6e61f1a7d26
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

Loading…