4-Aminopyridine → 4,4'-AZO-dipyridine

HRID 1448465Notes

Reaction equation

HRID 1448465 reaction equation
Cl[O-].[Na+].[NH2:4][C:5]1[CH:10]=[CH:9][N:8]=[CH:7][CH:6]=1>O>[N:4]([C:5]1[CH:10]=[CH:9][N:8]=[CH:7][CH:6]=1)=[N:4][C:5]1[CH:10]=[CH:9][N:8]=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 17274-AminopyridineHCID 23665760Sodium Hypochlorite2×

Product 1

HCID 2385894,4'-AZO-dipyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium hypochlorite, 1000 ml (5.25%, 0.72 mole) was added dropwise to a cold solution (5° C.) of 50 g (0.5 mole) of 4-aminopyridine in 400 ml water. The sodium hypochlorite was added at such a rate as to maintain the reaction temperature at less than 10° C. After the addition was completed, the reactants were stirred for an additional 11/2 hours at ~10° C. The resultant suspension was filtered and air dried to leave a crude brown solid. Recrystallization from methylcyclohexane yielded light orange crystals of 4,4'-azodipyridine, having a m.p. of 87°-89° C.

Workup

  1. temperatureto maintain the reaction temperature at less than 10° C
  2. additionAfter the addition
  3. filtrationThe resultant suspension was filtered
  4. customair dried
  5. customto leave a crude brown solid
  6. customRecrystallization from methylcyclohexane yielded light orange crystals of 4,4'-azodipyridine

Sources & evidence

ORD record
ord-8db8b7f32d814de5a480c203e0898c74
Source dataset
uspto-grants-1979_12
Patent number
US04180569

Reaction notes

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