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

HRID 1787728Notes

Reaction equation

HRID 1787728 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.O.[NH2:10][NH2:11]>O>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([NH:10][NH2:11])=[N:3][CH:4]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 27344145-Bromo-2-chloropyridine

Product 1

HCID 115356995-Bromo-2-hydrazinopyridineYield 83%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

2-Chloro-5-bromopyridine (64 g, 333 mmol) was suspended in hydrazine monohydrate (250 mL) and the mixture was heated at 70° C. for 72 hours. The reaction mixture was then diluted with water (750 mL) and the resulting precipitate was filtered off and azeotroped, firstly with toluene (×2) then dichloromethane (×2), to afford the title compound as a pale brown solid in 83% yield, 52 g.

Workup

  1. filtrationthe resulting precipitate was filtered off
  2. customazeotroped, firstly with toluene (×2)

Sources & evidence

ORD record
ord-564c8b5a3bae4c3eadeb4a04bda5ae70
Source dataset
uspto-grants-2009_03
Patent number
US07511057B2

Reaction notes

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