Sodium Hydroxide → 4,4'-Dichloro-2,2'-bipyridine

HRID 1867205Notes

Reaction equation

HRID 1867205 reaction equation
P(Cl)(Cl)Cl.[Cl:5][C:6]1[CH:7]=[C:8]([C:13]2[N+:14]([O-])=[CH:15][CH:16]=[C:17]([Cl:19])[CH:18]=2)[N+:9]([O-])=[CH:10][CH:11]=1.[OH-].[Na+]>C(Cl)(Cl)Cl>[Cl:19][C:17]1[CH:16]=[CH:15][N:14]=[C:13]([C:8]2[CH:7]=[C:6]([Cl:5])[CH:11]=[CH:10][N:9]=2)[CH:18]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24387Phosphorus trichlorideHCID 178526260HCID 178526260, compound

Product 1

HCID 1372004,4'-Dichloro-2,2'-bipyridine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
60 °C

Procedure

2 mL of chloroform, 0.326 mL of phosphorus trichloride and 0.082 g of 4,4′-dichloro-2,2′-bipyridyl-N,N′-dioxide were added to a 100 mL round bottom flask equipped with a condenser, and the mixture was refluxed in a hot water bath for 75 hours. The reaction solution was cooled with ice, poured into crushed ice and neutralized with 25% NaOH to pH 7 or higher. Chloroform was removed from the solution by distilling off under reduced pressure. The precipitated white powder was collected by filtration and washed with water. The powder was dissolved in a small amount of petroleum ether and recrystallized in a refrigerator overnight to give white needle crystal. The crystal was dried by heating to 60° C. under reduced pressure to give 4,4′-dichloro-2,2′-bipyridine.

Workup

  1. customequipped with a condenser
  2. temperaturethe mixture was refluxed in a hot water bath for 75 hours
  3. temperatureThe reaction solution was cooled with ice
  4. additionpoured
  5. custominto crushed ice
  6. customChloroform was removed from the solution
  7. distillationby distilling off under reduced pressure
  8. filtrationThe precipitated white powder was collected by filtration
  9. washwashed with water
  10. dissolutionThe powder was dissolved in a small amount of petroleum ether
  11. customrecrystallized in a refrigerator overnight
  12. customto give white needle crystal
  13. customThe crystal was dried

Sources & evidence

ORD record
ord-69c1889ea05e4ff39638d3d80d40e35b
Source dataset
uspto-grants-2009_12
Patent number
US07632600B2

Reaction notes

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