Nitric Acid → 5-Bromo-2-methyl-4-nitropyridine 1-oxide
Reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:9])=[N+:6]([O-:8])[CH:7]=1.S(=O)(=O)(O)O.[N+:15]([O-])([OH:17])=[O:16].C(=O)([O-])[O-].[Na+].[Na+]>>[Br:1][C:2]1[C:3]([N+:15]([O-:17])=[O:16])=[CH:4][C:5]([CH3:9])=[N+:6]([O-:8])[CH:7]=1Participants
5
Conditions
- Temperature
- 0 °C
Procedure
5-bromo-2-methylpyridine 1-oxide (2.269 g, 12.07 mmol, 1 eq) was dissolved in sulfuric acid (4 mL, 80 mmol, 6 eq) and cooled at 0° C. Fuming nitric acid (3 mL, 60 mmol, 5 eq) was added dropwise. After addition of the nitric acid was complete, the reaction mixture was first warmed to room temperature and then heated to 90° C. After 2 hours the reaction was cooled in an ice bath and slowly adjusted to pH 10 with 2 M aqueous sodium carbonate. This solution was extracted twice with dichloromethane. The combined organic extracts were dried over magnesium sulfate and concentrated to yield 2.54 g (90%) of 5-bromo-2-methyl-4-nitropyridine 1-oxide. LMCS (ESI) m+H=233.0.
Workup
- temperaturethe reaction mixture was first warmed to room temperature
- temperatureheated to 90° C
- temperatureAfter 2 hours the reaction was cooled in an ice bath
- extractionThis solution was extracted twice with dichloromethane
- dry with materialThe combined organic extracts were dried over magnesium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-d3f9b9e53c3447848a92c5aaf2e64872
- Source dataset
- uspto-grants-2015_04
- Patent number
- US08999998B2
Reaction notes
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