1: para-dicyanobenzene With sodium in ammonia T=-33°C; 2: benzonitrile in ammonia 0.5 h; 3: 1-bromo-butane in ammonia 1.5 h;

1: para-dicyanobenzene With sodium in ammonia T=-33°C; 2: 1-bromo-butane; benzonitrile in ammonia

acetic anhydride 2 h; Heating;

1: AlCl3 / CH2Cl2 / 5 h / Ambient temperature 2: 1) hydrazine hydrate, 2) KOH / 1) diethylene glycol, 130 deg C, 1 h, 2) diethylene glycol, 130 deg C, 2 h, then 160 deg C, 3 h 3: 1) TiCl4, 2) hydroxylamine hydrochloride, pyridine / 1) CH2Cl2, 0 deg C, 30 min, 2) ethanol, reflux, 2 h 4: 70 percent / acetic anhydride / 2 h / Heating View Scheme

1: 1) TiCl4, 2) hydroxylamine hydrochloride, pyridine / 1) CH2Cl2, 0 deg C, 30 min, 2) ethanol, reflux, 2 h 2: 70 percent / acetic anhydride / 2 h / Heating View Scheme

1: 1) hydrazine hydrate, 2) KOH / 1) diethylene glycol, 130 deg C, 1 h, 2) diethylene glycol, 130 deg C, 2 h, then 160 deg C, 3 h 2: 1) TiCl4, 2) hydroxylamine hydrochloride, pyridine / 1) CH2Cl2, 0 deg C, 30 min, 2) ethanol, reflux, 2 h 3: 70 percent / acetic anhydride / 2 h / Heating View Scheme

sodium hydroxide

formic acid; nickel monoaluminide 8 h; Heating;

1: aq. NaOH 2: H3BO3, H2SO4 View Scheme

1: aq. NaOH 2: (i) SOCl2, (ii) /BRN= 507924/, Py View Scheme