Pyridine-2-acetonitrile → HCID 178420215, compound

HRID 1756910Notes

Reaction equation

HRID 1756910 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][C:8]#[N:9].C([Sn]([N:23]=[N+:24]=[N-:25])(CCCC)CCCC)CCC>O1CCOCC1>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][C:8]1[NH:25][N:24]=[N:23][N:9]=1

Participants

4

Reactant 2

HCID 75959Pyridine-2-acetonitrileHCID 4984872Tributyltin azide

Product 1

HCID 178420215HCID 178420215, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2-Pyridylacetonitrile (10.0 g; 0.084 moles) was dissolved in p-dioxane (200 mL) and then treated with tributyltin azide (30.9 g; 0.093 moles) in one portion. The solution was refluxed for 20 hours, cooled to room temperature, and then concentrated in vacuo. The viscous syrup was taken up in ethyl ether and treated with gaseous HCl for over 15 minutes, affording a maroon-colored precipitate that was recrystallized from ethanol. Yield: 9.1 g (55%).

Workup

  1. temperatureThe solution was refluxed for 20 hours
  2. concentrationconcentrated in vacuo
  3. additiontreated with gaseous HCl for over 15 minutes
  4. customaffording a maroon-colored precipitate that
  5. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-63888c63e943476f9e11bafacff0eeda
Source dataset
uspto-grants-1995_08
Patent number
US05441975

Reaction notes

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