10 Pd/C; hydrogen in ethyl acetate

1: 1.) PhI(OCOCF3)2, 2.) (CH3)3SiN3 / 1.) (CF3)2CHOH, RT, 2.) (CF3)2CHOH, RT, 15 min 2: LiAlH4 / diethyl ether View Scheme

1: methanol; H2SO4 2: benzene; aqueous HNO3 3: Raney nickel; aqueous methanol.NaOH / Hydrogenation View Scheme

1: SnCl2; methanol. HCl 2: benzene; aqueous HNO3 3: Raney nickel; aqueous methanol.NaOH / Hydrogenation View Scheme

1: 1.) NaNO2/HCl; 50percent aq. KOH / 1.) H2O/EtOH, ice-cooling; 2.) EtOH, rt., 1 h 2: 0.273 g / HCl / ethanol / 5 h / Heating 3: 0.020 g / H2, CaO / 10percent Pd-C / ethanol / 60 - 70 °C 4: 0.102 g / sat. HCl / 30 h / Ambient temperature View Scheme

1: 1.) NaNO2/HCl; 50percent aq. KOH / 1.) H2O/EtOH, ice-cooling; 2.) EtOH, rt., 1 h 2: 0.273 g / HCl / ethanol / 5 h / Heating 3: 0.020 g / H2, CaO / 10percent Pd-C / ethanol / 60 - 70 °C View Scheme