triethylamine in N,N-dimethyl-formamide T=0 - 20°C; 24 h; Title compound not separated from byproducts;

triethylamine in ethanol 4 h; Ambient temperature;

1: conc. sulfuric acid / 0.25 h / 100 °C 2: 1.) aq. HCl, NaNO2, 2.) aq. NaN3, sodium acetate / 1.) 0 deg C, 15 min 3: toluene / 2 h / Heating 4: triethylamine / dimethylformamide / 24 h / 0 - 20 °C View Scheme

1: toluene / 2 h / Heating 2: triethylamine / dimethylformamide / 24 h / 0 - 20 °C View Scheme

1: acetic acid / 0.25 h / Heating 2: 60percent nitric acid, conc. sulfuric acid / 1.) 0 deg C, 10 min, 2.) RT, 30 min 3: conc. sulfuric acid / 0.25 h / 100 °C 4: 1.) aq. HCl, NaNO2, 2.) aq. NaN3, sodium acetate / 1.) 0 deg C, 15 min 5: toluene / 2 h / Heating 6: triethylamine / dimethylformamide / 24 h / 0 - 20 °C View Scheme

1: 60percent nitric acid, conc. sulfuric acid / 1.) 0 deg C, 10 min, 2.) RT, 30 min 2: conc. sulfuric acid / 0.25 h / 100 °C 3: 1.) aq. HCl, NaNO2, 2.) aq. NaN3, sodium acetate / 1.) 0 deg C, 15 min 4: toluene / 2 h / Heating 5: triethylamine / dimethylformamide / 24 h / 0 - 20 °C View Scheme

1: 1.) aq. HCl, NaNO2, 2.) aq. NaN3, sodium acetate / 1.) 0 deg C, 15 min 2: toluene / 2 h / Heating 3: triethylamine / dimethylformamide / 24 h / 0 - 20 °C View Scheme

triethylamine in N,N-dimethyl-formamide T=0 - 20°C; 24 h; Darkness;

1: NaClO; sodium hydroxide / methanol 2: triethylamine / N,N-dimethyl-formamide View Scheme