1,10-phenanthroline; triethyl amine hydrochloride in N,N-dimethyl-formamide T=20°C; 12 h; Inert atmosphere;

1: ethyl anthranilate With hydrogenchloride in water T=0°C; 0.0833333 h; Inert atmosphereSchlenk technique; 2: With tert.-butylnitrite T=0°C; 0.25 h; Inert atmosphereSchlenk technique; 3: trifluoromethylsilver T=-78 - 20°C; 4 h; Inert atmosphereSchlenk technique;

N,N'-dimethyl-N,N'-propyleneurea; 1,10-phenanthroline; Zn(2,2,6,6-tetramethylpiperidide)2; copper(l) chloride T=65°C; 24 h;

1: perfluoromethyl iodide; zinc With N,N'-dimethyl-N,N'-propyleneurea T=20°C; 2 h; Inert atmosphere; 2: 2-Iodo-benzoic acid ethyl ester With copper(l) iodide T=50°C; 24 h; Inert atmosphere; Catalytic behaviorMechanism; Reagent/catalystSolventTemperatureTime; chemoselective reaction;

1: perfluoromethyl iodide; zinc With N,N'-dimethyl-N,N'-propyleneurea T=20°C; 2 h; Inert atmosphere; 2: 2-Iodo-benzoic acid ethyl ester With copper(l) iodide; 1,10-phenanthroline T=50°C; 24 h; Inert atmosphere; Catalytic behavior; Reagent/catalystTemperature; chemoselective reaction;

Titanium(IV) oxide; trifluoroacetic acid in acetonitrile 24 h; Ambient temperatureIrradiation; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

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hydrazine