1.1: acetic anhydride / 110 °C 2.1: 85 percent / aq. nitric acid / acetic acid / 8 h / 45 - 50 °C 3.1: FeCl3; hydrazine hydrate / H2O; methanol / 3 h / Heating 3.2: 81 percent / HCl / H2O / 90 - 130 °C 4.1: 94 percent / thionyl chloride / dimethylformamide / 2 h / Heating 5.1: 80 percent / dimethylformamide / 1 h / 80 °C View Scheme

1.1: hydroxylamine hydrochloride; pyridine / methanol / Heating 2.1: acetic anhydride / 110 °C 3.1: 85 percent / aq. nitric acid / acetic acid / 8 h / 45 - 50 °C 4.1: FeCl3; hydrazine hydrate / H2O; methanol / 3 h / Heating 4.2: 81 percent / HCl / H2O / 90 - 130 °C 5.1: 94 percent / thionyl chloride / dimethylformamide / 2 h / Heating 6.1: 80 percent / dimethylformamide / 1 h / 80 °C View Scheme

1.1: 98 percent / potassium carbonate / dimethylformamide / 100 °C 2.1: hydroxylamine hydrochloride; pyridine / methanol / Heating 3.1: acetic anhydride / 110 °C 4.1: 85 percent / aq. nitric acid / acetic acid / 8 h / 45 - 50 °C 5.1: FeCl3; hydrazine hydrate / H2O; methanol / 3 h / Heating 5.2: 81 percent / HCl / H2O / 90 - 130 °C 6.1: 94 percent / thionyl chloride / dimethylformamide / 2 h / Heating 7.1: 80 percent / dimethylformamide / 1 h / 80 °C View Scheme

1.1: phosphorous pentoxide / anhydrous xylene / 18 h / Reflux 2.1: nitric acid / acetic acid / 4 h / 0 °C 3.1: sodium dithionite / water / 3 h / 50 °C 3.2: 0.5 h / 65 °C 4.1: acetic acid; N,N-dimethyl-formamide dimethyl acetal / toluene / 4 h / 105 °C 5.1: acetic acid / toluene / 5 h / 60 °C 6.1: toluene / 5 h / 125 °C 7.1: hydrogenchloride / methanol / 0.05 h / 15 - 20 °C View Scheme

1.1: urea / 0.5 h / 220 °C 2.1: phosphorous pentoxide / anhydrous xylene / 18 h / Reflux 3.1: nitric acid / acetic acid / 4 h / 0 °C 4.1: sodium dithionite / water / 3 h / 50 °C 4.2: 0.5 h / 65 °C 5.1: acetic acid; N,N-dimethyl-formamide dimethyl acetal / toluene / 4 h / 105 °C 6.1: acetic acid / toluene / 5 h / 60 °C 7.1: toluene / 5 h / 125 °C 8.1: hydrogenchloride / methanol / 0.05 h / 15 - 20 °C View Scheme

1: acetic acid / toluene / 5 h / 60 °C 2: toluene / 5 h / 125 °C 3: hydrogenchloride / methanol / 0.05 h / 15 - 20 °C View Scheme

1.1: tetra-(n-butyl)ammonium iodide; potassium carbonate / N,N-dimethyl-formamide / 1 h / 100 °C 1.2: 50 - 85 °C 2.1: water; potassium hydroxide / methanol / 4 h / 20 °C 3.1: urea / 0.5 h / 220 °C 4.1: phosphorous pentoxide / anhydrous xylene / 18 h / Reflux 5.1: nitric acid / acetic acid / 4 h / 0 °C 6.1: sodium dithionite / water / 3 h / 50 °C 6.2: 0.5 h / 65 °C 7.1: acetic acid; N,N-dimethyl-formamide dimethyl acetal / toluene / 4 h / 105 °C 8.1: acetic acid / toluene / 5 h / 60 °C 9.1: toluene / 5 h / 125 °C 10.1: hydrogenchloride / methanol / 0.05 h / 15 - 20 °C View Scheme

1.1: aq. NaOH / methanol / 0.5 h / 20 °C 1.2: 86 percent / methanol; H2O / 5 h / 25 °C 2.1: 90 percent / 3-ethynylaniline / propan-2-ol / 15 h / Heating View Scheme

in isopropyl alcohol 1.5 - 2 h; Heating / reflux; Product distribution / selectivity;

sodium hydroxide in water pH=5 - 12; Product distribution / selectivity;