1: hydroxylamine hydrochloride, pyridine / H2O / 1 h / Ambient temperature 2: CuSO4*5H2O, Et3N, DCC / CH2Cl2 / 2 h / Ambient temperature 3: 32 percent / n-Bu3SnH, AIBN / benzene / 5 h / Heating View Scheme

methanesulfonic acid T=90 - 95°C; 1 h; Yield given. Yields of byproduct given;

1.1: hydrazine hydrate / diethylene glycol / 0.5 h / 20 °C 1.2: 120 - 215 °C 2.1: AlCl3, aluminium chloride / tetrachloroethane, 1,1,2,2- / 20 °C / Cooling with ice 3.1: hydrazine hydrate / diethylene glycol / 0.5 h / 20 °C 3.2: 120 - 215 °C 4.1: sulfuric acid / Reflux 5.1: palladium 10 on activated carbon / triglyme (triethylene glycol dimethyl ether) / 4 h / 240 °C / Inert atmosphere 6.1: methanesulfonic acid / 0.5 h / 90 °C / Inert atmosphere View Scheme

1.1: methanesulfonic acid / 0.5 h / 90 °C / Inert atmosphere 2.1: hydrazine hydrate / diethylene glycol / 0.5 h / 20 °C 2.2: 120 - 215 °C 3.1: AlCl3, aluminium chloride / tetrachloroethane, 1,1,2,2- / 20 °C / Cooling with ice 4.1: hydrazine hydrate / diethylene glycol / 0.5 h / 20 °C 4.2: 120 - 215 °C 5.1: sulfuric acid / Reflux 6.1: palladium 10 on activated carbon / triglyme (triethylene glycol dimethyl ether) / 4 h / 240 °C / Inert atmosphere 7.1: methanesulfonic acid / 0.5 h / 90 °C / Inert atmosphere View Scheme

1.1: hydrazine hydrate / diethylene glycol / 0.5 h / 20 °C 1.2: 120 - 215 °C 2.1: methanesulfonic acid / 0.5 h / 90 °C / Inert atmosphere 3.1: hydrazine hydrate / diethylene glycol / 0.5 h / 20 °C 3.2: 120 - 215 °C 4.1: AlCl3, aluminium chloride / tetrachloroethane, 1,1,2,2- / 20 °C / Cooling with ice 5.1: hydrazine hydrate / diethylene glycol / 0.5 h / 20 °C 5.2: 120 - 215 °C 6.1: sulfuric acid / Reflux 7.1: palladium 10 on activated carbon / triglyme (triethylene glycol dimethyl ether) / 4 h / 240 °C / Inert atmosphere 8.1: methanesulfonic acid / 0.5 h / 90 °C / Inert atmosphere View Scheme

1.1: AlCl3, aluminium chloride / tetrachloroethane, 1,1,2,2- 2.1: hydrazine hydrate / diethylene glycol / 0.5 h / 20 °C 2.2: 120 - 215 °C 3.1: methanesulfonic acid / 0.5 h / 90 °C / Inert atmosphere 4.1: hydrazine hydrate / diethylene glycol / 0.5 h / 20 °C 4.2: 120 - 215 °C 5.1: AlCl3, aluminium chloride / tetrachloroethane, 1,1,2,2- / 20 °C / Cooling with ice 6.1: hydrazine hydrate / diethylene glycol / 0.5 h / 20 °C 6.2: 120 - 215 °C 7.1: sulfuric acid / Reflux 8.1: palladium 10 on activated carbon / triglyme (triethylene glycol dimethyl ether) / 4 h / 240 °C / Inert atmosphere 9.1: methanesulfonic acid / 0.5 h / 90 °C / Inert atmosphere View Scheme

permanganate(VII) ion; acetone

1: sodium; isoamyl alcohol 2: chromic acid; acetic acid View Scheme

chromic acid; acetic acid

Multistep reaction;