Hydrazine → 2'-Hydrazino-2,4'-bipyridine

HRID 465120Notes

Reaction equation

HRID 465120 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[CH:5]=[CH:4][N:3]=1.[NH2:14][NH2:15]>N1C=CC=CC=1>[NH:14]([C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[CH:5]=[CH:4][N:3]=1)[NH2:15]

Participants

4

Reactant 2

HCID 9321Hydrazine2×HCID 132987272′-Chloro-2,4′-bipyridine

Product 1

HCID 135337172'-Hydrazino-2,4'-bipyridine

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 5.0 g of 2'-chloro-2,4'-bipyridine, 5 ml of anhydrous hydrazine and 100 ml of pyridine was refluxed. Additional 5 ml portions of anhydrous hydrazine were added after 18, 36 and 54 hours of refluxing. The solution was then refluxed for an additional 48 hours and the solvent removed under vacuum. The solid was dissolved in methylene chloride, treated with activated carbon, filtered and the filtrate concentrated to dryness. The residue was triturated with hexane, giving crystals which were recrystallized from methylene chloride-hexane, giving 2'-hydrazino-2,4'-bipyridine as yellow crystals, mp 120°-121° C.

Workup

  1. temperaturewas refluxed
  2. temperatureof refluxing
  3. temperatureThe solution was then refluxed for an additional 48 hours
  4. customthe solvent removed under vacuum
  5. dissolutionThe solid was dissolved in methylene chloride
  6. additiontreated with activated carbon
  7. filtrationfiltered
  8. concentrationthe filtrate concentrated to dryness
  9. customThe residue was triturated with hexane
  10. customgiving crystals which
  11. customwere recrystallized from methylene chloride-hexane

Sources & evidence

ORD record
ord-7374b81c7b8a4ec48b361259b01a6de6
Source dataset
uspto-grants-1985_10
Patent number
US04550166

Reaction notes

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