1: glutaric acid anhydride; 2-fluoro-5-nitro-phenylamine With hydrogenchloride in toluene T=85°C; 4 h; 2: methylamine in water T=75°C; 3 h;

1: in water T=75°C; 3 h; 2: With hydrogenchloride in water T=55 - 60°C;

1.1: toluene / 4 h / 70 - 85 °C 2.1: water / 3 h / 75 °C 2.2: 55 - 60 °C View Scheme

1.1: toluene / 4 h / 70 - 85 °C 2.1: water / 3 h / 75 °C 2.2: 55 - 60 °C View Scheme

1: sulfuric acid / 10 h / |Reflux 2: iron sulphate heptahydrate; hydrogen; Iron (III) nitrate nonahydrate; 5 Pd/C / ethanol / 3000.3 Torr 3: potassium carbonate / water / 13.5 h / 69 - 70 °C / pH 4.2 - 5.5 / |Large scale View Scheme

sulfuric acid 10 h; Reflux;

1: sulfuric acid / 10 h / |Reflux 2: iron sulphate heptahydrate; hydrogen; Iron (III) nitrate nonahydrate; 5 Pd/C / ethanol / 3000.3 Torr 3: potassium carbonate / water / 13.5 h / 69 - 70 °C / pH 4.2 - 5.5 / |Large scale 4: thionyl chloride / dichloromethane / 17 h / -1 - 22 °C 5: hydrogenchloride / water; acetone / 40 - 75 °C View Scheme

1: sulfuric acid / 10 h / |Reflux 2: 5 Pd/C-iron; hydrogen / ethanol / 3000.3 Torr View Scheme

1: sulfuric acid / 10 h / |Reflux 2: 5 Pd/C-iron; hydrogen / ethanol / 3000.3 Torr 3: potassium iodide; DAHP / water / 65 - 70 °C / pH 4.2 - 5.5 4: thionyl chloride / dichloromethane / 16 h / 5 - 20 °C View Scheme