1: n-butyllithium / tetrahydrofuran; diethyl ether; hexane / 1 h / -100 - -78 °C / Inert atmosphere; Cooling with liquid nitrogen/methanol 2: ammonium chloride / tetrahydrofuran; diethyl ether; hexane / 1 h / 20 °C / Inert atmosphere; Saturated solution 3: palladium 10 on activated carbon; sodium carbonate / ethylene glycol dimethyl ether; water / 40 - 45 °C / Inert atmosphere 4: hydrogenchloride; water / methanol / 12 h / 50 °C View Scheme

1: n-butyllithium / tetrahydrofuran; diethyl ether; hexane / 1 h / -100 - -78 °C / Inert atmosphere; Cooling with liquid nitrogen/methanol 2: ammonium chloride / tetrahydrofuran; diethyl ether; hexane / 1 h / 20 °C / Inert atmosphere; Saturated solution 3: palladium 10 on activated carbon; sodium carbonate / ethylene glycol dimethyl ether; water / 40 - 45 °C / Inert atmosphere 4: hydrogenchloride; water / methanol / 12 h / 50 °C 5: 2,3-dicyano-5,6-dichloro-p-benzoquinone / tetrahydrofuran / 0.75 h / 60 °C / Inert atmosphere View Scheme