Pyridine-2-acetonitrile → HCID 178420215, compound

HRID 264054Notes

Reaction equation

HRID 264054 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-c0377c9ee2cc4fde8bff1170f9dcbbcf
Source dataset
uspto-grants-1997_07
Patent number
US05646170

Reaction notes

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