hydrogen; palladium on activated charcoal in ethanol

1: in toluene Reflux; 2: With hydrogenchloride; water T=20°C; Reflux;

1: With hydrogenchloride in water 5 h; Heating / reflux; 2: With sodium hydroxide in water

1.1: triethylamine / ethanol / 20 °C 2.1: sodium hydride / various solvent(s); methanol / 0 °C 2.2: dimethylsulfoxide / 70 °C 3.1: 0.95 g / hydrogen / Pd/C / ethanol View Scheme

1.1: lithium aluminium tetrahydride / diethyl ether / 5 h / 20 °C / |Inert atmosphere; |Cooling with ice 2.1: ethanol / |Inert atmosphere; |Reflux 3.1: sodium methylate / toluene / 0.33 h / |Inert atmosphere 3.2: 13 h / 60 °C / |Inert atmosphere 4.1: hydrogenchloride; zinc / ethanol; water / 20 °C / |Cooling with ice View Scheme

para-dicyanobenzene; ammonia in water; acetonitrile Addition; 1 h; Irradiation;

1: BuLi / tetrahydrofuran 2: p-dicyanobenzene; NH3 / acetonitrile; H2O / 1 h / Irradiation View Scheme

para-dicyanobenzene; ammonia in water; acetonitrile Addition; elimination; 4 h; Irradiation; Title compound not separated from byproducts;

Acetylation;