Nitric Acid → 5-Hydroxy-6-nitro-2-trifluoromethyl-quinoline-7-carboxylic acid methyl ester

反応式

[CH3:1][O:2][C:3]([C:5]1[CH:14]=[C:13]2[C:8]([CH:9]=[CH:10][C:11]([C:15]([F:18])([F:17])[F:16])=[N:12]2)=[C:7]([OH:19])[CH:6]=1)=[O:4].[N+:20]([O-])([OH:22])=[O:21].CCCCCC.C(OCC)(=O)C>S(=O)(=O)(O)O>[CH3:1][O:2][C:3]([C:5]1[CH:14]=[C:13]2[C:8]([CH:9]=[CH:10][C:11]([C:15]([F:18])([F:16])[F:17])=[N:12]2)=[C:7]([OH:19])[C:6]=1[N+:20]([O-:22])=[O:21])=[O:4]

参加物

実験手順

5-Hydroxy-2-trifluoromethyl-quinoline-7-carboxylic acid methyl ester (46.0 g) is dissolved in concentrated sulfuric acid (200 mL, 97%) at 0-5° C. To this cooled solution is added drop wise fuming nitric acid (7 mL, 100%). After the addition is complete, the reaction mixture is allowed to warm to room temperature. TLC analysis (hexane/ethyl acetate=4:1) after 30 min shows reaction completion. The reaction mixture is slowly poured onto an ice/water mixture (ca. 2 mL) and the crystals were filtered off, washed thoroughly with water and dried in vacuum to afford 47.0 g of the title compound of the formula