Nitric Acid → 4,5-Dibromo-6-nitropyridazin-3(2H)-one

HRID 2092097Notes

Reaction equation

HRID 2092097 reaction equation
[Br:1][C:2]1[C:3](=[O:9])[NH:4][N:5]=[CH:6][C:7]=1[Br:8].[N+:10]([O-])([OH:12])=[O:11]>S(=O)(=O)(O)O>[Br:1][C:2]1[C:3](=[O:9])[NH:4][N:5]=[C:6]([N+:10]([O-:12])=[O:11])[C:7]=1[Br:8]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 2361814,5-Dibromo-2,3-dihydropyridazin-3-one

Product 1

HCID 217841584,5-Dibromo-6-nitropyridazin-3(2H)-oneYield 93.5%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To 4,5-dibromopyridazin-3(2H)-one (2 g, 7.87 mmol) in concentrated sulfuric acid (12 mL), fuming nitric acid (978 μL, 23.8 mmol) was gradually added at 100° C. with stirring, and the resulting reaction solution was stirred at 100° C. for 3 hours. After completion of the reaction, the reaction solution was cooled to room temperature and poured onto ice-cold water. The precipitated crystals were collected by filtration and dried under reduced pressure to give the desired product (2.2 g, 93%).

Workup

  1. customthe resulting reaction solution
  2. stirringwas stirred at 100° C. for 3 hours
  3. customAfter completion of the reaction
  4. additionpoured onto ice-cold water
  5. filtrationThe precipitated crystals were collected by filtration
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-14c3f33e90d74c61b4f2fb53feed750a
Source dataset
uspto-grants-2013_05
Patent number
US08440666B2

Reaction notes

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