1: With ammonium acetate; sodium cyanoborohydride in methanol T=20°C; 2: With sodium hydroxide; water pH=13;

in methanol; toluene; mineral oil

1: anhydrous xylene / 20 h / 140 °C / |Inert atmosphere; |Schlenk technique 2: sodium hydroxide / butan-1-ol / 12 h / |Inert atmosphere; |Schlenk technique; |Reflux 3: copper(l) iodide; potassium carbonate; N-methyl-2-(methylamino)ethylamine / 1,4-dioxane / 20 h / 20 - 100 °C / |Inert atmosphere; |Schlenk technique View Scheme

1: anhydrous xylene / 20 h / 140 °C / |Inert atmosphere; |Schlenk technique 2: sodium hydroxide / butan-1-ol / 12 h / |Inert atmosphere; |Schlenk technique; |Reflux 3: copper(l) iodide; potassium carbonate; N-methyl-2-(methylamino)ethylamine / 1,4-dioxane / 20 h / 20 - 100 °C / |Inert atmosphere; |Schlenk technique 4: hydrazine hydrate; anhydrous iron chloride; carbon / water / 80 °C / |Inert atmosphere; |Schlenk technique View Scheme

1: Methyltriphenylphosphonium bromide With n-butyllithium in tetrahydrofuran T=0°C; 1 h; 2: 1-Pyrazin-2yl-ethanone in tetrahydrofuran T=20°C; 18 h;