1: 50 percent / aq. NaNO2, H2SO4, ethanol / benzene / 24 h / Heating 2: NBS, benzoyl peroxide / 1,2-dichloro-ethane / 6 h / Heating 3: 1.) hexamethylenetetraamine, 2.) AcOH, aq. HCl / 1.) CHCl3, reflux, 15 h, 2.) reflux, 30 min View Scheme

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1.1: trifluoroacetic acid; sodium nitrite / H2O / 0.17 h / 0 °C 1.2: 65 percent / sodium azide / H2O / 16 h / 20 °C 2.1: 90 percent / H2; Et3N / 10percent Pd/C / methanol / 1.25 h / 20 °C / 760.05 Torr View Scheme

ethanol; sulfuric acid; sodium nitrite in benzene 24 h; Heating;