1: H2 / 5percent Pd/C / dimethylformamide / 2 h / 2585.7 Torr 2: 1.) 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride, 2.) aq. NaOH / 1.) DMF, RT, 3 h, 2.) reflux, 1 h View Scheme

1: acetic anhydride / 2 h / 80 °C 2: aq. NaOH / methanol / 0.5 h 3: 82.6 percent / glacial acetic acid, aq. HCl, NaNO2 / H2O / 0.5 h 4: H2 / 5percent Pd/C / dimethylformamide / 2 h / 2585.7 Torr 5: 1.) 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride, 2.) aq. NaOH / 1.) DMF, RT, 3 h, 2.) reflux, 1 h View Scheme

1: 82.6 percent / glacial acetic acid, aq. HCl, NaNO2 / H2O / 0.5 h 2: H2 / 5percent Pd/C / dimethylformamide / 2 h / 2585.7 Torr 3: 1.) 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride, 2.) aq. NaOH / 1.) DMF, RT, 3 h, 2.) reflux, 1 h View Scheme

1: aq. NaOH / methanol / 0.5 h 2: 82.6 percent / glacial acetic acid, aq. HCl, NaNO2 / H2O / 0.5 h 3: H2 / 5percent Pd/C / dimethylformamide / 2 h / 2585.7 Torr 4: 1.) 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride, 2.) aq. NaOH / 1.) DMF, RT, 3 h, 2.) reflux, 1 h View Scheme

T=300°C;

1: 110 - 140 °C 2: 300 °C View Scheme

sodium hydroxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride 1.) DMF, RT, 3 h, 2.) reflux, 1 h; Yield given. Multistep reaction;