1: 5-nitro-1,2,3,4-tetrahydroquinoline With sodium hydride in dichloromethane; mineral oil 0.5 h; Inert atmosphere; 2: acetyl chloride in dichloromethane; mineral oil T=30°C; 48 h; Inert atmosphere;

1: pyridine / dichloromethane / 1 h / 0 - 25 °C 2: nitric acid; acetic anhydride / 4 h / -10 - 25 °C View Scheme

nitric acid; acetic anhydride T=-10 - 25°C; 4 h;

tin(ll) chloride in ethanol T=70°C; 22 h;

hydrogenchloride in ethanol; water 4 h; Reflux;