Nitric Acid → 3-Bromo-4-nitropyridine N-oxide
Reaction equation
[N+:1]([O-:4])(O)=[O:2].[Br:5][C:6]1[CH:7]=[N+:8]([O-:12])[CH:9]=[CH:10][CH:11]=1.[OH-].[Na+]>S(=O)(=O)(O)O>[Br:5][C:6]1[CH:7]=[N+:8]([O-:12])[CH:9]=[CH:10][C:11]=1[N+:1]([O-:4])=[O:2]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
Concentrated nitric acid (128 ml) and concentrated sulfuric acid (77 ml) were slowly added to a solution of 3-bromopyridin-N-oxide (31.9 g, 181.0 mmol) prepared in Step 1 in concentrated sulfuric acid (77 ml), while maintaining the temperature at 0° C.˜5° C. The reaction mixture was stirred at 90° C. for 2 hours and then cooled to room temperature. The reaction mixture was added to 1000 ml of ice water, which was then brought to pH 8 with 50% sodium hydroxide solution. The resulting precipitate was filtered and dried to give the titled compound as a yellow solid (29.3 g, 72.0%).
Workup
- temperaturewhile maintaining the temperature at 0° C.˜5° C
- temperaturecooled to room temperature
- filtrationThe resulting precipitate was filtered
- customdried
Sources & evidence
- ORD record
- ord-d38b85ffe98449859dbb57a838188dc3
- Source dataset
- uspto-grants-2009_06
- Patent number
- US07541366B2
Reaction notes
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