Nitric Acid → HCID 178526837, compound
Reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[C:4]([OH:9])=[N:5][CH:6]=[CH:7][CH:8]=1.S(=O)(=O)(O)O.[N+:17]([O-])([OH:19])=[O:18]>>[N+:17]([C:7]1[CH:8]=[C:3]([C:2]([F:1])([F:10])[F:11])[C:4]([OH:9])=[N:5][CH:6]=1)([O-:19])=[O:18]Participants
4
Conditions
- Temperature
- 0 °C
Procedure
3-(Trifluoromethyl)pyridin-2-ol (2.3 g) was added to concentrated sulfuric acid (15 mL) at 0° C. The mixture was stirred at 0° C. for 5 minutes. To this solution was added fuming nitric acid (6 mL) dropwise over 5 minutes. The reaction mixture was stirred at room temperature for 2 hours, and then heated at 50° C. for 3 hours. After cooling, the reaction mixture was poured onto ice (200 g), and the mixture was extracted with ethyl acetate three times. The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated under reduced pressure to provide the title compound.
Workup
- stirringThe reaction mixture was stirred at room temperature for 2 hours
- temperatureheated at 50° C. for 3 hours
- temperatureAfter cooling
- additionthe reaction mixture was poured onto ice (200 g)
- extractionthe mixture was extracted with ethyl acetate three times
- washThe combined organic layers were washed with brine
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-dda35ac380954eff9314af5a57f566c9
- Source dataset
- uspto-grants-2015_05
- Patent number
- US09034875B2
Reaction notes
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