1: 1.) sodium / 1.) ethanol, 45 deg C, 1 h, 2.)a) ethanol, 20 h , RT, b) 40 deg C, 4 h 2: 64 percent / 37percent HCl / 6 h / Heating View Scheme

1: 4-chloro-aniline With BCl3*Me2S in 1,2-dichloro-ethane T=0°C; Inert atmosphere; 2: chloroacetonitrile With AlCl3, aluminium chloride in 1,2-dichloro-ethane T=0°C; Friedel-Crafts acylation; Inert atmosphereReflux; 3: With hydrogenchloride; water in 1,2-dichloro-ethane

hydrogenchloride; water in n-heptane; benzene T=80°C; 0.5 h;