[BrH:1].S(=O)(=O)(O)O.[F:7][C:8]([F:24])([F:23])[C:9]1[CH:18]=[C:17]2[C:12]([C:13]([NH:19][CH2:20][CH2:21]O)=[CH:14][CH:15]=[N:16]2)=[CH:11][CH:10]=1.C([O-])(O)=O.[Na+]>O>[F:7][C:8]([F:24])([F:23])[C:9]1[CH:18]=[C:17]2[C:12]([C:13]([NH:19][CH2:20][CH2:21][Br:1])=[CH:14][CH:15]=[N:16]2)=[CH:11][CH:10]=1
Hydrobromic acid (0.88 ml, 16.2 mmol) and then sulphuric acid (0.29 ml, 5.5 mmol) are added dropwise to the 7-trifluoromethyl-4-(β-hydroxyethylamino)quinoline 10 (0.67 g, 2.6 mmol), the reaction medium being refrigerated using a bath of cold water. The reaction medium is then heated at 165° C. for 3 h 30 min, and then poured into 10 ml of cold water. The pH is then adjusted by adding NaHCO3 (pH approximately 9) and the medium is then extracted at the reflux of toluene (10 ml) for 15 min. The organic phase is then collected and the product 11 is obtained by crystallization at −18° C. overnight, filtration, and then drying under vacuum: 0.48 g (yield=58%). Mp: 106° C. (decomp.).
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