Hydrazine → [2,4'-Bipyridin]-5-amine

HRID 1594386Notes

Reaction equation

HRID 1594386 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)=[N:8][CH:9]=1)([O-])=O.NN>[Pd].C(O)C>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)=[N:8][CH:9]=1

Participants

5

Reactant 2

HCID 9321HydrazineHCID 111832665-nitro-2,4'-bipyridine

Product 1

HCID 45788763[2,4'-Bipyridin]-5-amineYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

5-Nitro-2,4′-bipyridine (10 g) obtained in Example 1 was added to ethanol (400 ml). 10% Pd—C (50% wet with water) (0.14 g) was added, and then, hydrazine.monohydrate (10 g) was dropwise added, for reflux under heating for 3 hours. The reaction solution was filtered and concentrated. The resulting crystal was recrystallized in ethyl acetate, to obtain the object substance (8.13 g; yield of 95%).

Workup

  1. temperaturefor reflux
  2. temperatureunder heating for 3 hours
  3. filtrationThe reaction solution was filtered
  4. concentrationconcentrated
  5. customThe resulting crystal was recrystallized in ethyl acetate
  6. customto obtain the object substance (8.13 g; yield of 95%)

Sources & evidence

ORD record
ord-61da0351d59f4790a6623ea520f41c84
Source dataset
uspto-grants-2007_11
Patent number
US07301029B2

Reaction notes

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