Sodium Hydroxide → 2-Bromo-3,3'-bipyridine

HRID 465130Notes

Reaction equation

HRID 465130 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[C:8](=O)[NH:9][CH:10]=[CH:11][CH:12]=2)[CH:2]=1.[OH-].[Na+].P(Br)(Br)([Br:18])=O>>[Br:18][C:8]1[C:7]([C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)=[CH:12][CH:11]=[CH:10][N:9]=1

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 24613Phosphorus oxybromideHCID 135337213-(3-pyridinyl)-2(1H)pyridinone

Product 1

HCID 135337192-Bromo-3,3'-bipyridine

Procedure

A mixture of 0.30 g of 3-(3-pyridinyl)-2(1H)pyridinone and 10 ml of phosphorus oxybromide was heated on a steam bath for 18 hours, then poured onto crushed ice and made alkaline with 10N sodium hydroxide. The resulting solid was collected, dissolved in methylene chloride and the solution passed through a short pad of hydrous magnesium silicate. The filtrate was concentrated and while boiling diluted with hexane. Concentration and chilling gave 2'-bromo-3,3'-bipyridine as white crystals, mp 97°-98° C.

Workup

  1. temperaturewas heated on a steam bath for 18 hours
  2. additionpoured
  3. customonto crushed ice
  4. customThe resulting solid was collected
  5. dissolutiondissolved in methylene chloride
  6. concentrationThe filtrate was concentrated
  7. additionwhile boiling diluted with hexane
  8. concentrationConcentration
  9. temperaturechilling

Sources & evidence

ORD record
ord-b11575c0cb7548709b94151f7fc3e5c5
Source dataset
uspto-grants-1985_10
Patent number
US04550166

Reaction notes

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