4-Methylpyridine → 4,4'-Dimethyl-2,2'-bipyridine

HRID 2394798Notes

Reaction equation

HRID 2394798 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH3:7])=[CH:3][CH:2]=1>[Pd].C1C=CC=CC=1>[CH3:7][C:4]1[CH:5]=[CH:6][N:1]=[C:2]([C:2]2[CH:3]=[C:4]([CH3:7])[CH:5]=[CH:6][N:1]=2)[CH:3]=1

Participants

4

Reactant 1

HCID 79634-Methylpyridine

Product 1

HCID 143384,4'-Dimethyl-2,2'-bipyridine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 241BenzeneSolvent

Procedure

Freshly distilled 4-picoline (600 ml) was refluxed with palladium on carbon 10% (w/v) for five days. The mixture was then refluxed for a further hour after addition of 100 ml of hot benzene. The palladium on carbon was then removed by filtration (glass-fibre paper). The filtration was repeated until a clear yellow solution was obtained. The volume of the solution was reduced by rotary evaporation of about 200 ml. and was left to stand for 24 hours. White crystals appeared which, after collection, were recrystalised from ethyl acetate. A colourless solid was recovered.

Workup

  1. temperatureThe mixture was then refluxed for a further hour
  2. customThe palladium on carbon was then removed by filtration (glass-fibre paper)
  3. filtrationThe filtration
  4. customwas obtained
  5. customThe volume of the solution was reduced by rotary evaporation of about 200 ml
  6. waitand was left
  7. customafter collection
  8. customwere recrystalised from ethyl acetate
  9. customA colourless solid was recovered

Sources & evidence

ORD record
ord-7f0666d31af54f798907b4a2452c7dc7
Source dataset
uspto-grants-1998_09
Patent number
US05811526

Reaction notes

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