[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH:6]=[C:5]2[C:13]([F:16])([F:15])[F:14].[N:17]([O-])=O.[Na+].O.O.Cl[Sn]Cl.NN>Cl.O>[NH:1]([C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH:6]=[C:5]2[C:13]([F:16])([F:14])[F:15])[NH2:17]In a 250 mL r.b. flask a suspension of 6-amino-4-trifluoromethylquinolin-2(1H)-one (structure 8 of Scheme II, where R1=trifluoromethyl) (2.28 g, 10 mmol) in 10 mL conc. HCl was cooled to −1° C. and a solution of NaNO2 (0.40 g, 12 mmol) in water (5 mL) was added dropwise in 20 min. The dark yellow suspension was stirred at −1° C. for 1 h and then a solution of SnCl2.2H2O (5.2 g, 15 mmol) in conc. HCl (10 mL) was added dropwise in 10 min. The light yellow suspension of the hydrazine was stirred at −1° C. for 2 h and then used directly or kept in a refrigerator at −1° C. until it was used (the crude compound can be stored for at least one month without decomposition).
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