Nitric Acid → 3-(1-Methyl-4-nitro-1h-pyrazol-3-yl)-2-oxazolidinone
Reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:11][CH2:10][O:9][C:8]2=[O:12])=[N:3]1.[N+:13]([O-])([OH:15])=[O:14].[OH-].[Na+]>S(=O)(=O)(O)O>[CH3:1][N:2]1[CH:6]=[C:5]([N+:13]([O-:15])=[O:14])[C:4]([N:7]2[CH2:11][CH2:10][O:9][C:8]2=[O:12])=[N:3]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 3-(1-methyl-1H-pyrazol-3-yl)-1,3-oxazolidin-2-one (85 mg) in conc. sulfuric acid (2.5 mL) was added fuming nitric acid (32 μL) under ice-cooling, and the mixture was stirred at 0° C. for 2 hr. The reaction mixture was neutralized with 8M aqueous sodium hydroxide solution under ice-cooling, and extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (methanol/ethyl acetate) to give the title compound (58 mg).
Workup
- temperaturecooling
- temperaturecooling
- extractionextracted with ethyl acetate
- washThe extract was washed with saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- customthe solvent was evaporated under reduced pressure
- customThe residue was purified by silica gel column chromatography (methanol/ethyl acetate)
Sources & evidence
- ORD record
- ord-2e340d326eed4ec4bb67f39ca00be91a
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09321757B2
Reaction notes
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