1.1: hydrogenchloride; water 2.1: nitric acid / water 3.1: hydrazine hydrate; acetic acid / water 4.1: butan-1-ol; water 5.1: hydrogenchloride; hydrogen / palladium on carbon / water; methanol 6.1: sodium dithionite / N,N-dimethyl-formamide / 90 °C 6.2: 95 - 105 °C View Scheme

1: 54.6 percent / conc. HCl, water / Heating 2: 98 percent / nitric acid / 0.5 h / -15 - -10 °C 3: 98 percent / hydrazine hydrate / acetic acid / 2.5 h / 100 °C 4: 86 percent / butan-1-ol / 20 h / Heating 5: 88.6 percent / H2, 1N aq. HCL / 5percent Pd/C / methanol / 2 h View Scheme

1: 54.6 percent / conc. HCl, water / Heating 2: 98 percent / nitric acid / 0.5 h / -15 - -10 °C 3: 98 percent / hydrazine hydrate / acetic acid / 2.5 h / 100 °C View Scheme

1: 54.6 percent / conc. HCl, water / Heating 2: 98 percent / nitric acid / 0.5 h / -15 - -10 °C 3: 98 percent / hydrazine hydrate / acetic acid / 2.5 h / 100 °C 4: 86 percent / butan-1-ol / 20 h / Heating View Scheme

1: 54.6 percent / conc. HCl, water / Heating 2: 98 percent / nitric acid / 0.5 h / -15 - -10 °C View Scheme

hydrogenchloride; water Heating;