pyridine in tetrachloromethane T=55 - 60°C; 6 h;

in toluene T=-10°C; Acylation; 5 h;

in benzene 1.) 100 deg C, 13 h, 2.) RT, 18 h;

1: 95 percent / triethylamine / toluene / 12 h / 20 °C 2: benzyltriethylammonium tribromide; ZnCl2 / acetic acid / 5 h / 60 °C 3: 95 percent / Zn; acetic acid / 24 h / 80 °C 4: 85 percent / LiAlH4 / tetrahydrofuran / 0 - 20 °C View Scheme

N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate; hydrazine hydrate in tetrachloromethane; dichloromethane T=20°C; 3 h;