1: 70 percent / N-methylpyrrolidine / 0.5 h / Heating 2: 96 percent / aqu NaOH, Br2 / dioxane / 50 - 60 °C 3: 1) SOCl2 / 1) DMF, 45 min, reflux; 2) benzene, 2 min, reflux 4: 1) HCl (g); 2) NH3 (g) / 1) chloroform, ethanol, 7 d; 2) ether, ethanol, 7 d View Scheme

1: 96 percent / aqu NaOH, Br2 / dioxane / 50 - 60 °C 2: 1) SOCl2 / 1) DMF, 45 min, reflux; 2) benzene, 2 min, reflux 3: 1) HCl (g); 2) NH3 (g) / 1) chloroform, ethanol, 7 d; 2) ether, ethanol, 7 d View Scheme

hydrogenchloride; ammonia 1) chloroform, ethanol, 7 d; 2) ether, ethanol, 7 d; Yield given. Multistep reaction;

1: 1) SOCl2 / 1) DMF, 45 min, reflux; 2) benzene, 2 min, reflux 2: 1) HCl (g); 2) NH3 (g) / 1) chloroform, ethanol, 7 d; 2) ether, ethanol, 7 d View Scheme