Hydrazine → 2-Hydrazino-3,3'-bipyridine

HRID 465131Notes

Reaction equation

HRID 465131 reaction equation
Br[C:2]1[C:7]([C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.[NH2:14][NH2:15]>N1C=CC=CC=1>[NH:14]([C:2]1[C:7]([C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)=[CH:6][CH:5]=[CH:4][N:3]=1)[NH2:15]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 135337192-Bromo-3,3'-bipyridine

Product 1

HCID 135337152-Hydrazino-3,3'-bipyridine

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 16.46 g of 2'-bromo-3,3'-bipyridine, 24 ml of anhydrous hydrazine and 500 ml of dry pyridine was heated at 100° C. for 3 days. The solvent was removed under vacuum, toluene was added and removed and the residue was partitioned between saturated aqueous sodium carbonate and methylene chloride. The organic layer was dried, the solvent removed under vacuum and the residue crystallized from methylene chloride-hexane, giving 2'-hydrazino-3,3'-bipyridine as tan crystals.

Workup

  1. customThe solvent was removed under vacuum, toluene
  2. additionwas added
  3. customremoved
  4. customthe residue was partitioned between saturated aqueous sodium carbonate and methylene chloride
  5. customThe organic layer was dried
  6. customthe solvent removed under vacuum
  7. customthe residue crystallized from methylene chloride-hexane

Sources & evidence

ORD record
ord-be94748dd56543058014dafbf39d5368
Source dataset
uspto-grants-1985_10
Patent number
US04550166

Reaction notes

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