Nitric Acid → 4-Nitro-2-(trifluoromethyl)pyridine 1-oxide
Reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N+:4]=1[O-:9].[N+:12]([O-])([OH:14])=[O:13]>OS(O)(=O)=O>[N+:12]([C:7]1[CH:6]=[CH:5][N+:4]([O-:9])=[C:3]([C:2]([F:1])([F:10])[F:11])[CH:8]=1)([O-:14])=[O:13]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 130 °C
Procedure
To a stirred solution of 2-trifluoromethyl-pyridine 1-oxide (0.43 g, 2.43 mmol) in concentrated H2SO4 (2 mL) is added 70% HNO3 (1.6 mL) dropwise at 0° C. Reaction mixture is allowed to stir for 2 h at 130° C. After completion of reaction it is quenched with ice (˜200 g) and pH is adjusted 7 with solid K2CO3 (15-20 g) and extracted with EtOAc (3×20 mL). Organic part is washed with water, brine and dried over anhydrous MgSO4. Solution is concentrated under reduced pressure. The residue is purified by column chromatography (silica-gel, 100-200 mesh, eluent; 20% EtOAc in hexane) to afford 4-nitro-2-trifluoromethyl-pyridine 1-oxide (0.1 g, 20%).
Workup
- customReaction mixture
- customAfter completion of reaction it
- customis quenched with ice (˜200 g) and pH
- extractionextracted with EtOAc (3×20 mL)
- washOrganic part is washed with water, brine
- dry with materialdried over anhydrous MgSO4
- concentrationSolution is concentrated under reduced pressure
- customThe residue is purified by column chromatography (silica-gel, 100-200 mesh, eluent; 20% EtOAc in hexane)
Sources & evidence
- ORD record
- ord-8c6fa616a71c4283a18cddeda04a926e
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08362249B2
Reaction notes
Loading…