1: 58 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene / dimethylformamide / 2 h 2: 93 percent / NaNO2 / H2O; dimethylformamide / 24 h / 80 - 90 °C 3: 80 percent / methanolic ammonia / dimethylformamide / 22 h / 130 °C / a sealed, glass-lined steel bomb 4: 85 percent / H2 / PtO2 / ethanol; ethyl acetate / 0.5 h / 1520 Torr / Ambient temperature 5: acetic anhydride / 1 h / Heating View Scheme

1: 93 percent / NaNO2 / H2O; dimethylformamide / 24 h / 80 - 90 °C 2: 80 percent / methanolic ammonia / dimethylformamide / 22 h / 130 °C / a sealed, glass-lined steel bomb 3: 85 percent / H2 / PtO2 / ethanol; ethyl acetate / 0.5 h / 1520 Torr / Ambient temperature 4: acetic anhydride / 1 h / Heating View Scheme

1: 80 percent / methanolic ammonia / dimethylformamide / 22 h / 130 °C / a sealed, glass-lined steel bomb 2: 85 percent / H2 / PtO2 / ethanol; ethyl acetate / 0.5 h / 1520 Torr / Ambient temperature 3: acetic anhydride / 1 h / Heating View Scheme

1: 85 percent / H2 / PtO2 / ethanol; ethyl acetate / 0.5 h / 1520 Torr / Ambient temperature 2: acetic anhydride / 1 h / Heating View Scheme

acetic anhydride 1 h; Heating;

1: amonium sulfate / Heating 2: 48 percent / stannic chloride / 1,2-dichloro-ethane / 3 h / Ambient temperature 3: 1.) BCl3; 2.) CH3OH / 1.) CH2Cl2, -78 deg C, 2 h; 2.) -78 deg C, 2 h, room temp. 30 min. 4: 60 percent / phosphorus pentasulfide / pyridine; H2O / 12 h / Heating 5: 1.) 1N NaOH; 2.) 1N NaOH / 1.) aq. ethanol, room temp., 2 h; 2.) room temp., 1 h. 6: 30 percent / NH3 (l) / 4 h / 150 °C / steel bomb View Scheme

1: amonium sulfate / Heating 2: 40 percent / stannic chloride / 1,2-dichloro-ethane / 3 h / Ambient temperature 3: 1.) BCl3; 2.) CH3OH / 1.) CH2Cl2, -78 deg C, 2 h; 2.) -78 deg C, 2 h, room temp. 30 min. 4: 60 percent / phosphorus pentasulfide / pyridine; H2O / 12 h / Heating 5: 1.) 1N NaOH; 2.) 1N NaOH / 1.) aq. ethanol, room temp., 2 h; 2.) room temp., 1 h. 6: 42 percent / NH3 (l) / 4 h / 150 °C / steel bomb View Scheme