Ammonia → 5-Methylpicolinonitrile

HRID 1366241Notes

Reaction equation

HRID 1366241 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].N>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

5

Reactant 3

HCID 222AmmoniaHCID 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 ammonia 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-25499428e62647afb746157f05e24a02
Source dataset
uspto-grants-2011_02
Patent number
US07893073B2

Reaction notes

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