2-Bromo-5-methylpyridine → 5-Methylpicolinonitrile

HRID 1766361Notes

Reaction equation

HRID 1766361 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][N:3]=1.[Cu](C#N)[C:10]#[N:11]>CN(C)C=O>[CH3:8][C:5]1[CH:6]=[CH:7][C:2]([C:10]#[N:11])=[N:3][CH:4]=1

Participants

4

Reactant 2

HCID 5642162-Bromo-5-methylpyridineHCID 178418260HCID 178418260, compound

Product 1

HCID 741835-Methylpicolinonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

36 g (209 mmol) 2-Bromo-5-methylpyridine and 37.5 g (418 mmol) copper cyanide are refluxed for two hours in 500 ml dimethylformamide. After cooling down to 50° C., 10% aqueous armnoia solution (500 ml) is added with stirring. The product is extracted with dichloromethane, the organic phase is dried over magnesium sulfate, and the solvent is removed in vacuo. The product is purified by column chromatography (silica, eluent cyclohexane/ethyl acetate 9:1).

Workup

  1. extractionThe product is extracted with dichloromethane
  2. dry with materialthe organic phase is dried over magnesium sulfate
  3. customthe solvent is removed in vacuo
  4. customThe product is purified by column chromatography (silica, eluent cyclohexane/ethyl acetate 9:1)

Sources & evidence

ORD record
ord-aa5d72989a7d490caf21a27f46842892
Source dataset
uspto-grants-2007_06
Patent number
US07230017B2

Reaction notes

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