triethylsilane; t-Bu-P4 in hexane; N,N-dimethyl-formamide T=80°C; 24 h;

1: 9.2 g / H2 / 10percent Pd-C / ethyl acetate / 4 h / Ambient temperature 2: 1.) 12 N HCl, NaNO2, 2.) Na2CO3 / 1.) H2O, 2-3 deg C, 20 min, 2.a) H2O, 1.5 h, 3 deg C, b.) 2 h, 50 deg C View Scheme

1: 1.) NaH / 1.) DMF, 30 min, room temperature, 2.a) DMF, 30 min, room temperature, b.) 2 h, 90 deg C 2: 9.2 g / H2 / 10percent Pd-C / ethyl acetate / 4 h / Ambient temperature 3: 1.) 12 N HCl, NaNO2, 2.) Na2CO3 / 1.) H2O, 2-3 deg C, 20 min, 2.a) H2O, 1.5 h, 3 deg C, b.) 2 h, 50 deg C View Scheme

1: 1.) NaH / 1.) DMF, 30 min, room temperature, 2.a) DMF, 30 min, room temperature, b.) 2 h, 90 deg C 2: 9.2 g / H2 / 10percent Pd-C / ethyl acetate / 4 h / Ambient temperature 3: 1.) 12 N HCl, NaNO2, 2.) Na2CO3 / 1.) H2O, 2-3 deg C, 20 min, 2.a) H2O, 1.5 h, 3 deg C, b.) 2 h, 50 deg C View Scheme

hydrogenchloride; sodium carbonate; sodium nitrite 1.) H2O, 2-3 deg C, 20 min, 2.a) H2O, 1.5 h, 3 deg C, b.) 2 h, 50 deg C; Yield given. Multistep reaction;

hydrogen sulfide; triethylamine in N,N-dimethyl-formamide T=90°C; 0.5 h;