Nitric Acid → 3-Nitro-5-(trifluoromethyl)pyridin-2-amine
Reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[CH:5][C:6]([NH2:9])=[N:7][CH:8]=1.[N+:12]([O-])([OH:14])=[O:13]>S(=O)(=O)(O)O.CCOC(C)=O>[N+:12]([C:5]1[C:6]([NH2:9])=[N:7][CH:8]=[C:3]([C:2]([F:1])([F:10])[F:11])[CH:4]=1)([O-:14])=[O:13]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 70 °C
Procedure
To a solution of 5-(trifluoromethyl)pyridine-2-amine (1.1 g, 6.79 mmol) dissolved in sulfuric acid (20 mL) at room temperature was added nitric acid (0.475 g, 6.79 mmol). After heating to 70° C. for 1 hr, the reaction mixture was cooled to room temperature and diluted with EtOAc and ice. The organic layer was separated, washed with sat. sodium bicarbonate aq. and brine, dried over anhydrous Na2SO4, filtered, concentrated under reduced pressure and chromatographed on silica gel eluting with a gradient solvent mixture (5% MeOH-DCM to 15% MeOH-DCM) to give the title compound (680 mg). LC/MS: m/z 208(M+H). 1H-NMR (500 MHz, CD3OD): δ 8.60 (d, 1H), 8.67 (d, 1H).
Workup
- temperaturethe reaction mixture was cooled to room temperature
- customThe organic layer was separated
- washwashed with sat. sodium bicarbonate aq. and brine
- dry with materialdried over anhydrous Na2SO4
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customchromatographed on silica gel eluting with a gradient solvent mixture (5% MeOH-DCM to 15% MeOH-DCM)
Sources & evidence
- ORD record
- ord-a0216e4887f640b8b7a10907cc643a57
- Source dataset
- uspto-grants-2011_09
- Patent number
- US08017605B2
Reaction notes
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