sodium hydroxide in methanol T=20°C;

1: 98 percent / N-bromosuccinimide; 2,2'-azobisisobutyronitrile / CH2Cl2 / 16 h / Heating 2: 81 percent / ammonia / methanol / 2 h / 20 °C 3: 83 percent / ammonium formate / Pd/C / dimethylformamide / 0.5 h / 100 °C 4: aq. NaHCO3 / ethyl acetate / 0.5 h / 20 °C 5: NaOH / methanol / 20 °C View Scheme

1: 81 percent / ammonia / methanol / 2 h / 20 °C 2: 83 percent / ammonium formate / Pd/C / dimethylformamide / 0.5 h / 100 °C 3: aq. NaHCO3 / ethyl acetate / 0.5 h / 20 °C 4: NaOH / methanol / 20 °C View Scheme

1: 83 percent / ammonium formate / Pd/C / dimethylformamide / 0.5 h / 100 °C 2: aq. NaHCO3 / ethyl acetate / 0.5 h / 20 °C 3: NaOH / methanol / 20 °C View Scheme

1: aq. NaHCO3 / ethyl acetate / 0.5 h / 20 °C 2: NaOH / methanol / 20 °C View Scheme