1: With potassium hydroxide in ethylene glycol T=20°C; Wolff-Kishner reduction; 1 h; Inert atmosphere; 2: With hydrazine hydrate T=185°C; Wolff-Kishner reduction; 1.75 h; Inert atmosphere;

1.1: n-butyllithium / tetrahydrofuran; diethyl ether / 0.25 h / -78 °C / Inert atmosphere 1.2: 2 h / -78 °C / Inert atmosphere 2.1: potassium hydroxide / ethylene glycol / 1 h / 20 °C / Inert atmosphere 2.2: 1.75 h / 185 °C / Inert atmosphere View Scheme

1.1: n-butyllithium / tetrahydrofuran; diethyl ether / 0.25 h / -78 °C / Inert atmosphere 1.2: 2 h / -78 °C / Inert atmosphere 2.1: potassium hydroxide / ethylene glycol / 1 h / 20 °C / Inert atmosphere 2.2: 1.75 h / 185 °C / Inert atmosphere View Scheme

1: water / 2 h 2: hydrogenchloride; sodium nitrite / water / 5 °C 3: methanol / 10 h / 20 °C / Reflux View Scheme

1: hydrogenchloride; sodium nitrite / water / 5 °C 2: methanol / 10 h / 20 °C / Reflux View Scheme