Nitric Acid → N-[2-Nitro-4-[1-(trifluoroacetyl)-2-pyrrolidinyl]-5-fluorophenyl]trifluoroacetamide
Reaction equation
[N+:1]([O-:4])(O)=[O:2].[F:5][C:6]([F:29])([F:28])[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([CH:16]2[CH2:20][CH2:19][CH2:18][N:17]2[C:21](=[O:26])[C:22]([F:25])([F:24])[F:23])=[C:12]([F:27])[CH:11]=1)=[O:8]>O>[F:29][C:6]([F:5])([F:28])[C:7]([NH:9][C:10]1[CH:11]=[C:12]([F:27])[C:13]([CH:16]2[CH2:20][CH2:19][CH2:18][N:17]2[C:21](=[O:26])[C:22]([F:23])([F:24])[F:25])=[CH:14][C:15]=1[N+:1]([O-:4])=[O:2])=[O:8]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
100 ml of fuming nitric acid was added to 28 g of 2,2,2-trifluoro-N-(3-fluoro-4-(1-(trifluoroacetyl)pyrrolidin-2-yl)phenyl)acetamide with cooling with ice, and the reaction liquid was stirred at room temperature for 1 hour. Water with ice was added to the reaction liquid to dilute it, then extracted with ethyl acetate, washed with saturated saline, and dried with anhydrous magnesium sulfate. The solvent was evaporated away under reduced pressure, and the resulting residue was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate=10/1) to obtain the entitled compound as a yellow oily substance.