1: aq. NaOH / methanol / Heating 2: 43 percent / NaH / dimethylformamide / 100 °C 3: 69 percent / H2 / Pd/C View Scheme

1.1: 6.52 g / aq. NaOH / methanol / 3 h / Heating 2.1: 78 percent / NaH / dimethylformamide / 3 h / 100 °C 3.1: 96 percent / H2 / Pd/C / methanol / 3.5 h / 20 °C / 760 Torr 4.1: iodine monochloride / methanol / 2 h / 20 °C 4.2: 70 percent / aq. ammonia / methanol View Scheme

1: aq. NaOH / methanol / Heating 2: 43 percent / NaH / dimethylformamide / 100 °C View Scheme