Acetaldehyde → 2-Acetylpyridine-4-carbonitrile

HRID 1491833Notes

Reaction equation

HRID 1491833 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]#[N:8])=[CH:3][CH:2]=1.[CH:9](=[O:11])[CH3:10].S(=O)(=O)(O)O>O.C(OO)(C)(C)C>[C:9]([C:2]1[CH:3]=[C:4]([C:7]#[N:8])[CH:5]=[CH:6][N:1]=1)(=[O:11])[CH3:10]

Participants

6

Reactant 3

HCID 177AcetaldehydeHCID 1118Sulfuric AcidHCID 75064-Cyanopyridine

Product 1

HCID 104644602-Acetylpyridine-4-carbonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6410tert-Butyl hydroperoxideSolvent

Procedure

A solution of ferrous sulfate heptahydrate (496 g) in water (1080 ml) and tert-butylhydroperoxide (173 ml) were simultaneously added to a solution of 4-pyridinecarbonitrile (30 g), acetaldehyde (97.6 ml) and sulfuric acid (15.4 ml) in water (90 ml) at 0° C. with stirring. After stirring at the same temperature for one hour, the resulting precipitate was collected by filtration and washed with water to give 2-acetyl-4-pyridinecarbonitrile (22.5 g).

Workup

  1. stirringAfter stirring at the same temperature for one hour
  2. filtrationthe resulting precipitate was collected by filtration
  3. washwashed with water

Sources & evidence

ORD record
ord-b17636ae0e1e40ffaf2ce73b3a0f9c5c
Source dataset
uspto-grants-1994_12
Patent number
US05371097

Reaction notes

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