Hydrazine hydrate (1:1) → 5-Bromo-2-hydrazinopyridine

HRID 1437261Notes

Reaction equation

HRID 1437261 reaction equation
O.[NH2:2][NH2:3].Br[C:5]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][N:6]=1>N1C=CC=CC=1>[Br:11][C:8]1[CH:9]=[CH:10][C:5]([NH:2][NH2:3])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 693532,5-Dibromopyridine

Product 1

HCID 115356995-Bromo-2-hydrazinopyridine

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Hydrazine monohydrate (10 mL) was added to 2,5-dibromopyridine (10.0 g) in pyridine (100 mL) at room temperature, and the resultant mixture was refluxed under heat for 13 hours, and then cooled in air. The reaction solvent was removed under reduced pressure, and the residue was partitioned by use of aqueous 0.5N sodium hydroxide and chloroform. The organic layer was dried over sodium sulfate anhydrate, followed by filtration. The solvent was removed under reduced pressure, to thereby give 5-bromo-2-hydrazinopyridine as a solid (7.61 g, 96%).

Workup

  1. temperatureunder heat for 13 hours
  2. temperaturecooled in air
  3. customThe reaction solvent was removed under reduced pressure
  4. customthe residue was partitioned by use of aqueous 0.5N sodium hydroxide and chloroform
  5. dry with materialThe organic layer was dried over sodium sulfate anhydrate
  6. filtrationfollowed by filtration
  7. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-a26c68f1f2fc44d29d28d580baf106e5
Source dataset
uspto-grants-2009_11
Patent number
US07622471B2

Reaction notes

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