Potassium Nitrate → 5-Nitro-2-(trifluoromethyl)quinoline
Reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1.[N+:15]([O-])([O-:17])=[O:16].[K+]>S(=O)(=O)(O)O>[N+:15]([C:9]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:10]=1[CH:11]=[CH:12][C:3]([C:2]([F:1])([F:13])[F:14])=[N:4]2)([O-:17])=[O:16]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
1.52 g (7.7 mmol) of 2-(trifluoromethyl)quinoline is dissolved in 7.90 ml of concentrated sulfuric acid, and 1.47 g of potassium nitrate is added in portions at 0° C. After 20 hours at room temperature, the reaction solution is poured onto ice/water. It is extracted with ethyl acetate, the combined organic phases are washed with saturated sodium bicarbonate solution and dried on sodium sulfate. After removal of the solvent and chromatography on silica gel with hexane-ethyl acetate (10-100%), 390 mg (21% of theory) of the product is obtained.