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

HRID 465119Notes

Reaction equation

HRID 465119 reaction equation
[NH:1]1[C:6](=O)[CH:5]=[CH:4][CH:3]=[C:2]1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1.P(Cl)(Cl)([Cl:16])=O>>[Cl:16][C:6]1[N:1]=[C:2]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[CH:3]=[CH:4][CH:5]=1

Participants

3

Reactant 2

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

Product 1

HCID 111168506-CHLORO-2,2'-BIPYRIDINE

Procedure

To 100 ml of phosphorus oxychloride, cooled in an ice bath, was added 5.3 g of [2,2'-bipyridin]-6(1H)-one. The mixture was warmed to room temperature and then heated on a steam bath for 18 hours, then concentrated under vacuum. Crushed ice was added to the residual oil and the solution was basified with solid potassium carbonate. This mixture was extracted with methylene chloride, the extract was dried and evaporated in vacuo to a solid This solid was dissolved in ethyl acetate and placed on a silica gel column. The column was eluted with ethyl acetate and the obtained solid recrystallized from heptane, giving 6'-chloro-2,2'-bipyridine as white crystals, mp 60°-62° C., which was then treated as described in Example 1, giving the desired product.

Workup

  1. temperatureheated on a steam bath for 18 hours
  2. concentrationconcentrated under vacuum
  3. additionCrushed ice was added to the residual oil
  4. extractionThis mixture was extracted with methylene chloride
  5. customthe extract was dried
  6. customevaporated in vacuo to a solid This solid
  7. dissolutionwas dissolved in ethyl acetate
  8. washThe column was eluted with ethyl acetate
  9. customthe obtained solid recrystallized from heptane

Sources & evidence

ORD record
ord-a6fc40ee6f04408cbdf4e3249a03c3b6
Source dataset
uspto-grants-1985_10
Patent number
US04550166

Reaction notes

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