SnCl2·2H2O; 1,8-diazabicyclo[5.4.0]undec-7-ene in toluene 8 h; Reflux;

1 h; Heating;

1: 82 percent / 1 h / Heating 2: 88 percent / 4percent KOH / ethanol / 0.33 h / Heating 3: 1.) aq. NaOH / 1.) C2H5OH, reflux, 1 h, 2.) C2H5OH, reflux, 3 h View Scheme

potassium carbonate; tetrabutylammomium bromide in tetrahydrofuran T=20°C; 6.66667 h; 3;

hydrogen; nickel

1: N-chloro-succinimide / N,N-dimethyl-formamide / 5 h / 20 °C 2: triethylamine / N,N-dimethyl-formamide / 48 h / 20 °C / Inert atmosphere 3: chloro-trimethyl-silane View Scheme

1: 4-hydroxyphenylbenzakdehyde oxime With hydrogenchloride; N-chloro-succinimide in N,N-dimethyl-formamide T=20°C; 3.5 h; 2: methylene hexane With triethylamine in N,N-dimethyl-formamide T=0 - 20°C; 14.5 h;

1: 1.) N-chlorosuccinimide, pyridine; 2.) Et3N / 1.) chloroform, 60 deg C, 30 min; 2.) 40-50 deg C, 20 min 2: 88 percent / hydrogen / W-2 Raney nickel / methanol; aq. acetic acid / 5 h / Ambient temperature 3: 77 percent / 99percent hydrazine hydrate / aq. ethanol / 2 h / Ambient temperature 4: 80 percent / 10percent HCl / aq. ethanol / 2 h / Heating View Scheme