Nitric Acid → 7-Fluoro-5-nitroindolin-2-one
Reaction equation
[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][C:8](=[O:11])[CH2:7]2.[N+:12]([O-])([OH:14])=[O:13]>OS(O)(=O)=O>[F:1][C:2]1[CH:3]=[C:4]([N+:12]([O-:14])=[O:13])[CH:5]=[C:6]2[C:10]=1[NH:9][C:8](=[O:11])[CH2:7]2Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -45 °C
Procedure
7-fluoro-1,3-dihydro-2H-indol-2-one (8.0 g, 52.9 mmol) was slurried in H2SO4 (conc., 86 ml) and the mixture cooled to −45° C. A solution of fuming nitric acid (>90%, 3.34 g, 52.9 mmol) in H2SO4 (20 ml) was added drop wise, while maintaining the temperature at −45° C. throughout the addition. The mixture was allowed to slowly warm to RT and stirred overnight. The mixture was poured into stirred ice-cold water (1500 ml). A white precipitate resulted, and the slurry was aged at 0° C. for 1 hour. The solid was collected by filtration, triturated with cold water (2×), and dissolved into EtOAc (1 L). This solution was washed with basic brine (containing sodium bicarbonate), dried over Na2SO4, filtered, and the volatiles removed in vacuum to give the titled compound.
Workup
- temperaturewhile maintaining the temperature at −45° C.
- additionthroughout the addition
- temperatureto slowly warm to RT
- additionThe mixture was poured
- customA white precipitate resulted
- waitthe slurry was aged at 0° C. for 1 hour
- filtrationThe solid was collected by filtration
- customtriturated with cold water (2×)
- dissolutiondissolved into EtOAc (1 L)
- washThis solution was washed with basic brine (containing sodium bicarbonate)
- dry with materialdried over Na2SO4
- filtrationfiltered
- customthe volatiles removed in vacuum
Sources & evidence
- ORD record
- ord-1497be41017c4dbea3426e11dc2b938f
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08552022B2
Reaction notes
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