Dimethylformamide → 5-Methylpicolinonitrile

HRID 1835672Notes

Reaction equation

HRID 1835672 reaction equation
Br[C:2]1[N:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1.[CH3:9][N:10](C=O)C>ClCCl>[C:9]([C:2]1[N:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1)#[N:10]

Participants

4

Reactant 2

HCID 6228DimethylformamideHCID 5642162-Bromo-5-methylpyridine

Product 1

HCID 741835-MethylpicolinonitrileYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 6-bromo-3-picoline (3 g, 17.4 mmol) and cuprous cyanide (2.3 g, 26.1 mmol) in DMF (60 mL) was heated at reflux for 1.5 h. The reaction mixture was diluted with dichloromethane, washed with aqueous ammonia, dried over magnesium sulfate, and concentrated in vacuo. The residue was purified by column chromatography (EtOAc:n-hexane, 1:9) to give the title compound (1.6 g, 78%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1.5 h
  3. washwashed with aqueous ammonia
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography (EtOAc:n-hexane, 1:9)

Sources & evidence

ORD record
ord-bff9308b02c8477a922744b11f646372
Source dataset
uspto-grants-2004_08
Patent number
US06774110B2

Reaction notes

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