Nitric Acid → 2,6-Dibromo-4-nitro-1-oxo-1lambda~5~-pyridine
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[N+:3]=1[O-:9].[N+:10]([O-])([OH:12])=[O:11].[OH-].[Na+]>S(=O)(=O)(O)O>[N+:10]([C:6]1[CH:5]=[C:4]([Br:8])[N+:3]([O-:9])=[C:2]([Br:1])[CH:7]=1)([O-:12])=[O:11]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
2,6-dibromopyridine-N-oxide (6.28 g) was dissolved in concentrated sulphuric acid (20 ml) with stirring. A mixture of concentrated sulphuric acid (20 ml) and concentrated nitric acid (10 ml) was then continuously added dropwise. The solution was then heated at 90° C. for 3 hours with stirring, poured onto ice and then basified with sodium hydroxide. The solution was then continuously extracted with ether, and recrystallised from ethanol to give pale yellow leaflets of 4-nitro-2,6-dibromopyridine-N-oxide (1.2 g, 16%), m.p. 222° C.-224° C.
Workup
- additionwas then continuously added dropwise
- stirringwith stirring
- additionpoured onto ice
- extractionThe solution was then continuously extracted with ether
- customrecrystallised from ethanol
Sources & evidence
- ORD record
- ord-6e4d0d26b47540e584ee97bab27b8cff
- Source dataset
- uspto-grants-1999_07
- Patent number
- US05929082
Reaction notes
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