Nitric Acid → 5-nitro-2-(1,1,1-trifluoro-2-methylpropan-2-yl)pyridin-4(1H)-one
Reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]([C:6]1[NH:7][CH:8]=[CH:9][C:10](=[O:12])[CH:11]=1)([CH3:5])[CH3:4].OS(O)(=O)=O.[N+:20]([O-])([OH:22])=[O:21].[OH-].[Na+]>>[N+:20]([C:9]1[C:10](=[O:12])[CH:11]=[C:6]([C:3]([CH3:5])([CH3:4])[C:2]([F:1])([F:13])[F:14])[NH:7][CH:8]=1)([O-:22])=[O:21]Participants
5
Conditions
- Temperature
- 90 °C
Procedure
To a mixture of 2-(1,1,1-trifluoro-2-methylpropan-2-yl)pyridin-4(1H)-one (300 mg, 1.462 mmol) in H2SO4 (8 mL, 150 mmol) was added nitric acid (3.27 mL, 73.1 mmol). The mixture was stirred at 90° C. for 15 h. Then the mixture was added to ice water and basified by aqueous NaOH solution. The mixture was filtered. The filtrate was concentrated and purified by preparative TLC (DCM/MeOH=9:1, Rf=0.1) to yield a light yellow solid of 5-nitro-2-(1,1,1-trifluoro-2-methylpropan-2-yl)pyridin-4(1H)-one (100 mg, 0.380 mmol, 26.0% yield): 1H NMR (400 MHz, CD3OD): δ 8.82 (s, 1H), 6.95 (s, 1H), 1.64 (s, 6H). ES-LCMS m/z 251.1 (M+H).
Workup
- filtrationThe mixture was filtered
- concentrationThe filtrate was concentrated
- custompurified by preparative TLC (DCM/MeOH=9:1, Rf=0.1)
Sources & evidence
- ORD record
- ord-c7032ed2fb0c479b86e5a19883d19223
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09382238B2
Reaction notes
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