Phosphorus oxychloride → 6-CHLORO-2,2'-BIPYRIDINE

HRID 465107Notes

Reaction equation

HRID 465107 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[NH:8][C:9](=O)[CH:10]=[CH:11][CH:12]=1.P(Cl)(Cl)([Cl:16])=O>>[Cl:16][C:9]1[N:8]=[C:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)[CH:12]=[CH:11][CH:10]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 640070[2,2'-Bipyridin]-6(1H)-one

Product 1

HCID 111168506-CHLORO-2,2'-BIPYRIDINE

Procedure

A mixture of 5.3 g of 2-(2-pyridinyl)-6-(1H)-pyridinone and 100 ml of phosphorus oxychloride was heated on a steam bath for 18 hours and then concentrated to dryness under vacuum. Crushed ice was added to the oil residue and the mixture made basic with solid potassium carbonate. The mixture was then extracted with dichloromethane, the extracts treated with activated carbon, filtered and concentrated, giving a solid which was purified by chromatography on silica gel with ethyl acetate as solvent, giving 4.1 g of 6'-chloro-2,2'-bipyridine as white crystals, mp 60°-62° C.

Workup

  1. temperaturewas heated on a steam bath for 18 hours
  2. concentrationconcentrated to dryness under vacuum
  3. additionCrushed ice was added to the oil residue
  4. extractionThe mixture was then extracted with dichloromethane
  5. additionthe extracts treated with activated carbon
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customgiving a solid which
  9. customwas purified by chromatography on silica gel with ethyl acetate as solvent

Sources & evidence

ORD record
ord-1fe8c026342b42f9b2482fcc48ec443d
Source dataset
uspto-grants-1985_10
Patent number
US04550166

Reaction notes

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