Hydrazine hydrate (1:1) → 3-Bromo-4-hydrazinyl-5-nitropyridine

HRID 524919Notes

Reaction equation

HRID 524919 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([N+:9]([O-:11])=[O:10])[C:7]=1Cl.O.[NH2:13][NH2:14]>C(O)C>[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([N+:9]([O-:11])=[O:10])[C:7]=1[NH:13][NH2:14]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 125100523-Bromo-4-chloro-5-nitropyridine

Product 1

HCID 867209743-Bromo-4-hydrazinyl-5-nitropyridineYield 79.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3-bromo-4-chloro-5-nitro-pyridine (500 mg, 2.106 mmol), hydrazine hydrate (158.1 mg, 153.6 μL, 3.159 mmol) in ethanol (5.000 mL) was stirred at RT for 1 h. The bright yellow precipitate was filtered, washed with methanol and dried under vacuum to leave 3-bromo-4-hydrazinyl-5-nitropyridine (390 mg, 79.5%). MS (ES−) 232.8.

Workup

  1. filtrationThe bright yellow precipitate was filtered
  2. washwashed with methanol
  3. customdried under vacuum

Sources & evidence

ORD record
ord-ebf75cf6720f41cf88fa846234f5a511
Source dataset
uspto-grants-2016_05
Patent number
US09340546B2

Reaction notes

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