N,N,N',N'-tetra-methylnaphthalene-1,8-diamine in dichloromethane T=0 - 20°C; 1 h;

1: 100 percent / hydrogen, Adam's catalyst / 2585.7 Torr 2: thionyl chloride / toluene / 3 h / 55 - 60 °C 3: 1.) aq. sodium azide / 1.) acetone, 0 deg C, 0.5 h, 2.) toluene, 80 deg C, 0.5 h View Scheme

1: thionyl chloride / toluene / 3 h / 55 - 60 °C 2: 1.) aq. sodium azide / 1.) acetone, 0 deg C, 0.5 h, 2.) toluene, 80 deg C, 0.5 h View Scheme

1: 89 percent / piperidine / pyridine / 1.) 80 deg C, 1 h, 2.) 100 deg C, 1 h, 3.) heating, 0.5 h 2: 100 percent / hydrogen, Adam's catalyst / 2585.7 Torr 3: thionyl chloride / toluene / 3 h / 55 - 60 °C 4: 1.) aq. sodium azide / 1.) acetone, 0 deg C, 0.5 h, 2.) toluene, 80 deg C, 0.5 h View Scheme

1: 99 percent / 1.) HBr, aq. sodium nitrite, 2.) cuprous bromide / acetone / 1.) -5 deg C, 0.5 h, 2.) 25 deg C, 0.5 h 2: zinc / acetic acid / 1 h 3: 43 percent / aq. sodium hydroxide / 2 h / Heating 4: thionyl chloride / toluene / 3 h / 55 - 60 °C 5: 1.) aq. sodium azide / 1.) acetone, 0 deg C, 0.5 h, 2.) toluene, 80 deg C, 0.5 h View Scheme

1: 43 percent / aq. sodium hydroxide / 2 h / Heating 2: thionyl chloride / toluene / 3 h / 55 - 60 °C 3: 1.) aq. sodium azide / 1.) acetone, 0 deg C, 0.5 h, 2.) toluene, 80 deg C, 0.5 h View Scheme

1: zinc / acetic acid / 1 h 2: 43 percent / aq. sodium hydroxide / 2 h / Heating 3: thionyl chloride / toluene / 3 h / 55 - 60 °C 4: 1.) aq. sodium azide / 1.) acetone, 0 deg C, 0.5 h, 2.) toluene, 80 deg C, 0.5 h View Scheme

sodium azide 1.) acetone, 0 deg C, 0.5 h, 2.) toluene, 80 deg C, 0.5 h; Multistep reaction;