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

HRID 465113Notes

Reaction equation

HRID 465113 reaction equation
Cl[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 104200582-Chloro-3,3'-bipyridine

Product 1

HCID 135337152-Hydrazino-3,3'-bipyridine

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
110 °C

Procedure

A 440 mg portion of 2-chloro-3,3'-bipyridine and 0.73 ml of anhydrous hydrazine were dissolved in 15 ml of pyridine and heated at 110° C. for 3 days. The volatiles were removed at reduced pressure, 10 ml of toluene was added and the volatiles again removed. The residue was partitioned between 125 ml of methylene chloride and 25 ml of saturated aqueous sodium carbonate. The organic layer was dried and the solvent removed at reduced pressure, giving an oily solid which was recrystallized from methylene chloride-hexane, giving 2-hydrazino-3,3'-bipyridine as a tan powder, mp 104.5°-107° C.

Workup

  1. customThe volatiles were removed at reduced pressure, 10 ml of toluene
  2. additionwas added
  3. customthe volatiles again removed
  4. customThe residue was partitioned between 125 ml of methylene chloride and 25 ml of saturated aqueous sodium carbonate
  5. customThe organic layer was dried
  6. customthe solvent removed at reduced pressure
  7. customgiving an oily solid which
  8. customwas recrystallized from methylene chloride-hexane

Sources & evidence

ORD record
ord-502ee92532264767b2575038b721b5b4
Source dataset
uspto-grants-1985_10
Patent number
US04550166

Reaction notes

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