1: 0.5 N aq. barium hydroxide / Heating; overnight 2: Et3N / butan-1-ol / 48 h / Heating 3: 1.) 3 N HCl, sodium nitrite, 2.) sodium acetate trihydrate / 1.) water, 2.) acetic acid, water, RT, overnight View Scheme

1: 0.5 N aq. barium hydroxide / Heating; overnight 2: Et3N / butan-1-ol / 48 h / Heating 3: 1.) 3 N HCl, sodium nitrite, 2.) sodium acetate trihydrate / 1.) water, 2.) acetic acid, water, RT, overnight 4: 66 percent / Zn, acetic acid / H2O; ethanol / 3 h / Heating 5: 81 percent / sodium nitrite, acetic acid / H2O / 1 h / 0 °C 6: 83 percent / liquid ammonia / methanol / 20 h / 60 °C View Scheme

1: H2 / 10percent Pd/C / ethanol 2: 0.5 N aq. barium hydroxide / Heating; overnight 3: Et3N / butan-1-ol / 48 h / Heating 4: 1.) 3 N HCl, sodium nitrite, 2.) sodium acetate trihydrate / 1.) water, 2.) acetic acid, water, RT, overnight 5: 69 percent / Zn, acetic acid / H2O; ethanol / 3 h / Heating 6: 73 percent / 12 N HCl / overnight 7: 77 percent / 0.33 N aq. NaOH / 5 h / Heating View Scheme

1: H2 / 10percent Pd/C / ethanol 2: 0.5 N aq. barium hydroxide / Heating; overnight 3: Et3N / butan-1-ol / 48 h / Heating 4: 1.) 3 N HCl, sodium nitrite, 2.) sodium acetate trihydrate / 1.) water, 2.) acetic acid, water, RT, overnight 5: 69 percent / Zn, acetic acid / H2O; ethanol / 3 h / Heating 6: 82 percent / sodium nitrite, acetic acid / H2O / 1 h / 0 °C 7: 88 percent / liquid ammonia / methanol / 20 h / 60 °C View Scheme

1: H2 / 10percent Pd/C / ethanol 2: 0.5 N aq. barium hydroxide / Heating; overnight 3: Et3N / butan-1-ol / 48 h / Heating 4: 1.) 3 N HCl, sodium nitrite, 2.) sodium acetate trihydrate / 1.) water, 2.) acetic acid, water, RT, overnight 5: 69 percent / Zn, acetic acid / H2O; ethanol / 3 h / Heating 6: 82 percent / sodium nitrite, acetic acid / H2O / 1 h / 0 °C View Scheme

1: 0.5 N aq. barium hydroxide / Heating; overnight 2: Et3N / butan-1-ol / 48 h / Heating View Scheme

1: 0.5 N aq. barium hydroxide / Heating; overnight 2: Et3N / butan-1-ol / 48 h / Heating 3: 1.) 3 N HCl, sodium nitrite, 2.) sodium acetate trihydrate / 1.) water, 2.) acetic acid, water, RT, overnight 4: 66 percent / Zn, acetic acid / H2O; ethanol / 3 h / Heating 5: 81 percent / sodium nitrite, acetic acid / H2O / 1 h / 0 °C 6: 90 percent / 0.25 N aq. NaOH / 3 h / Heating View Scheme

1: 0.5 N aq. barium hydroxide / Heating; overnight 2: Et3N / butan-1-ol / 48 h / Heating 3: 1.) 3 N HCl, sodium nitrite, 2.) sodium acetate trihydrate / 1.) water, 2.) acetic acid, water, RT, overnight 4: 66 percent / Zn, acetic acid / H2O; ethanol / 3 h / Heating View Scheme

1: H2 / 10percent Pd/C / ethanol 2: 0.5 N aq. barium hydroxide / Heating; overnight 3: Et3N / butan-1-ol / 48 h / Heating 4: 1.) 3 N HCl, sodium nitrite, 2.) sodium acetate trihydrate / 1.) water, 2.) acetic acid, water, RT, overnight 5: 69 percent / Zn, acetic acid / H2O; ethanol / 3 h / Heating 6: 82 percent / sodium nitrite, acetic acid / H2O / 1 h / 0 °C 7: 81 percent / 0.25 N aq. NaOH / 3 h / Heating View Scheme

1: 98 percent / HCl / methanol / 1 h / Heating 2: 95 percent / Lithium triethylborohydride / tetrahydrofuran / 0.5 h / 0 °C 3: pyridine View Scheme