sulfuric acid; potassium nitrate 1.) 0 deg C, 1 h, 2.) room temperature, 2 h, 3.) 100 deg C, 5 h, 4.) 130 deg C, 4h;

1: 2-chloro-4-methyl-5-nitropyridine With tetrakis(triphenylphosphine) palladium(0) in 1,4-dioxane 0.25 h; 2: trimethylboroxine With potassium carbonate T=20°C; 22 h; Heating / reflux;

1: With nitric acid; trifluoroacetic anhydride 10 h; 2: With sodium disulfite 24 h;

1: 55 percent / SeO2 / dioxane / 4 h / Heating 2: 91 percent / p-toluenesulfonic acid monohydrate / toluene / Heating 3: 92 percent / H2 / 10percent Pd/C / 20 h / 2585.7 Torr View Scheme

1: 98 percent / H2 / 5percent Pd/C / ethanol / 2 h / 3102.9 Torr 2: 51 percent / 10percent aq. sulfuric acid, aq. sodium nitrite / a.) 0 deg C, 15 min, b.) reflux, 15 min View Scheme

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hydrogen; palladium on activated charcoal in ethanol P=3102.9 Torr; 2 h;

hydrogen; palladium in ethanol

1: 40 percent / SeO2 / dioxane / 3 h / Heating 2: 89 percent / p-toluenesulfonic acid monohydrate / toluene / Heating 3: 88 percent / potassium, EtOH / toluene / 2 h / Ambient temperature 4: 62 percent / H2 / 10percent Pd/C / CH2Cl2 / 2 h / 1551.4 Torr 5: 77 percent / p-toluenesulfonic acid monohydrate / acetonitrile; H2O / 5 h / Heating View Scheme