Nitric Acid → 4,6-Dihydroxy-5-nitro-2-trifluoromethyl-nicotinic acid ethyl ester
Reaction equation
[CH2:1]([O:3][C:4](=[O:17])[C:5]1[C:10]([OH:11])=[CH:9][C:8]([OH:12])=[N:7][C:6]=1[C:13]([F:16])([F:15])[F:14])[CH3:2].[N+:18]([O-])([OH:20])=[O:19]>S(=O)(=O)(O)O>[CH2:1]([O:3][C:4](=[O:17])[C:5]1[C:10]([OH:11])=[C:9]([N+:18]([O-:20])=[O:19])[C:8]([OH:12])=[N:7][C:6]=1[C:13]([F:14])([F:15])[F:16])[CH3:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
4,6-dihydroxy-2-trifluoromethyl-nicotinic acid ethyl ester (1 g, 3.9 mmol) was dissolved in 10 mL of concentrated sulfuric acid and 2 mL of fuming nitric acid was added dropwise at room temperature. Once the addition was complete, the mixture was stirred at room temperature for 30 minutes. The mixture was then poured into crushed ice and the white precipitate was collected, dissolved in 50 mL of ethyl acetate, washed with 50 mL of water and 50 mL of brine, dried over magnesium sulfate and the solvent was removed in vacuo to give 1.1 g of the title compound as a white solid.