sodium hydroxide in methanol 0.333333 h; Heating;

N-bromosuccinmide; dibenzoyl peroxide in tetrachloromethane 8 h; Heating;

1: 100 percent / pyridine / 3 h / Heating 2: 98 percent / N-bromsuccinimide, dibenzoylperoxide / CCl4 / 8 h / Heating View Scheme

1: 63 percent / 50 percent NaOH / methanol / 0.33 h / Heating 2: 1) KOH, NaOH; 2) H2SO4 / 1) 1 h, reflux, ethanol; water, room temp., 2) 1 h, reflux 3: 1) SOCl2 / 1) DMF, 45 min, reflux; 2) benzene, 2 min, reflux 4: 1) HCl (g); 2) NH3 (g) / 1) nitrobenzene, ethanol, 7 d; 2) ether, ethanol, 7 d View Scheme

1: 63 percent / 50 percent NaOH / methanol / 0.33 h / Heating 2: 1) KOH, NaOH; 2) H2SO4 / 1) 1 h, reflux, ethanol; water, room temp., 2) 1 h, reflux 3: 1) SOCl2 / 1) DMF, 45 min, reflux; 2) benzene, 2 min, reflux View Scheme