(Pyrazin-2-yl)acetonitrile → HCID 136359207, compound

HRID 2286259Notes

Reaction equation

HRID 2286259 reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[CH2:7][C:8]#[N:9].[N:10]([O-])=[O:11].[Na+]>C(O)(=O)C>[OH:11][N:10]=[C:7]([C:2]1[CH:3]=[N:4][CH:5]=[CH:6][N:1]=1)[C:8]#[N:9]

Participants

4

Reactant 2

HCID 12782906(Pyrazin-2-yl)acetonitrileHCID 23668193Sodium Nitrite

Product 1

HCID 136359207HCID 136359207, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Pyrazineacetonitrile (32 g), prepared as described in British Patent Specification No. 1 021 397, was dissolved in glacial acetic acid (250 ml). The solution was stirred and 1.2 equivalents of sodium nitrite (22.3 g) were added in small portions, while the temperature was kept under 20° C. After the addition, the reaction mixture was stirred at room temperature for another two hours. The title compound separated partly from the reaction mixture. On evaporation of the solvent under reduced pressure, a solid was obtained which on recrystallization from hot water yielded α-hydroxyiminopyrazineacetonitrile (35 g, 88%). Melting point >192° C. (dec.).

Workup

  1. customwas kept under 20° C
  2. additionAfter the addition
  3. stirringthe reaction mixture was stirred at room temperature for another two hours
  4. customThe title compound separated partly from the reaction mixture
  5. customOn evaporation of the solvent under reduced pressure
  6. customa solid was obtained which
  7. customon recrystallization from hot water

Sources & evidence

ORD record
ord-ba42fb78d84b4530927d9718759347b2
Source dataset
uspto-grants-1982_04
Patent number
US04327213

Reaction notes

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