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

HRID 1081230

Reaction equation

HRID 1081230 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/w) 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 to 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 to 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-cf304c59b9324b78898d62d2ce935bc0
Source dataset
uspto-grants-1996_12
Patent number
US05585279

Linked notes

Loading…