1: With potassium carbonate in 1,4-dioxane; N,N-dimethyl-formamide T=72°C; 0.5 h; 2: With O-(4-nitrophenyl)hydroxylamine in 1,4-dioxane; N,N-dimethyl-formamide T=72°C; 20 h; Reagent/catalystTemperatureTime;

1.1: 1,2-dichloro-ethane / 4 h / Heating 1.2: 93 percent / dioxane / 4 h / 0 - 20 °C 2.1: 88 percent / potassium bis(trimethylsilyl)amide; 18-crown-6 / tetrahydrofuran; toluene / 1.5 h / Heating 3.1: 80 percent / sodium hydride; (2,4-dinitro-phenyl)-hydroxylamine / tetrahydrofuran / 1.5 h / Heating View Scheme

1: 88 percent / potassium bis(trimethylsilyl)amide; 18-crown-6 / tetrahydrofuran; toluene / 1.5 h / Heating 2: 80 percent / sodium hydride; (2,4-dinitro-phenyl)-hydroxylamine / tetrahydrofuran / 1.5 h / Heating View Scheme

1.1: oxalyl chloride; N,N-dimethylformamide / CH2Cl2 / 1.5 h / 20 °C 1.2: 100 percent / ammonia gas / CH2Cl2 / 2 h / 0 °C 2.1: 1,2-dichloro-ethane / 4 h / Heating 2.2: 93 percent / dioxane / 4 h / 0 - 20 °C 3.1: 88 percent / potassium bis(trimethylsilyl)amide; 18-crown-6 / tetrahydrofuran; toluene / 1.5 h / Heating 4.1: 80 percent / sodium hydride; (2,4-dinitro-phenyl)-hydroxylamine / tetrahydrofuran / 1.5 h / Heating View Scheme

1: lithium hexamethyldisilazane / tetrahydrofuran / 4.5 h / -13 - -5 °C 2: oxalyl dichloride / dichloromethane; N,N-dimethyl-formamide / 19 h / 20 °C 3: ammonia / tetrahydrofuran / -40 - 20 °C 4: oxalyl dichloride / 1,2-dichloro-ethane / 17 h / 20 °C / |Reflux 5: sodium hydride / toluene; ethylene glycol dimethyl ether; mineral oil / 46 h / -9 °C / |Reflux 6: potassium carbonate; O-(4-nitrophenyl)hydroxylamine / N,N-dimethyl-formamide; 1,4-dioxane / 22.5 h / 72 °C View Scheme

1: ammonia / tetrahydrofuran / -40 - 20 °C 2: oxalyl dichloride / 1,2-dichloro-ethane / 17 h / 20 °C / |Reflux 3: sodium hydride / toluene; ethylene glycol dimethyl ether; mineral oil / 46 h / -9 °C / |Reflux 4: potassium carbonate; O-(4-nitrophenyl)hydroxylamine / N,N-dimethyl-formamide; 1,4-dioxane / 22.5 h / 72 °C View Scheme