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 nitric acid (fuming) (6 mL) dropwise over 5 minutes. The reaction mixture was stirred at room temperature for 2 hours, and was heated at 50° C. for 3 hours. After cooling, the reaction mixture was poured into 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 give the title compound.
Workup
- stirringThe reaction mixture was stirred at room temperature for 2 hours
- temperaturewas heated at 50° C. for 3 hours
- temperatureAfter cooling
- 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-edd1abb222834b8f81800bcfbdf614f4
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08563735B2
Reaction notes
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