Water → 3-(2-Pyridinyl)Propanenitrile

HRID 499584

Reaction equation

HRID 499584 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1/[CH:7]=[CH:8]/[C:9]#[N:10].[BH4-].[Na+].O>CC(O)C>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][CH2:8][C:9]#[N:10]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 10866363(2E)-3-(pyridin-2-yl)prop-2-enenitrile

Product 1

HCID 146872203-(2-Pyridinyl)PropanenitrileYield 83.6%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
80 °C

Procedure

(E)-3-(2-Pyridyl)acrylonitrile (0.50 g, 3.8 mmol) was dissolved in 2-propanol (10 ml), and sodium borohydride (0.50 g, 13.2 mmol) was added thereto. The reaction mixture was stirred at 80° C. for 14 hrs and cooled under ice cooling condition, combined with water, concentrated to the half amount and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was subjected to a silica gel (25 g) column chromatography. The fractions eluted with hexane-ethyl acetate (1:1, v/v) were collected and concentrated to give the titled compound (0.42 g, 82%).

Workup

  1. temperaturecooled under ice cooling condition
  2. concentrationconcentrated to the half amount
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated
  7. washThe fractions eluted with hexane-ethyl acetate (1:1
  8. customv/v) were collected
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-72875183cd0e48b28547f39988f3e503
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Linked notes

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