in toluene

thionyl chloride in dichloromethane T=20°C; 2 h;

nitric acid in water T=40 - 45°C; 4.33333 - 4.5 h;

sodium hydroxide in toluene

1: 95 percent / K2CO3 / dimethylformamide / 10 h / 85 °C 2: 95 percent / aq. H2SO4; HNO3; AcOH / 50 h / 20 °C 3: 75 percent / sodium dithionite / H2O / 20 - 50 °C 4: 38 percent / KOH / 2-methyl-butan-2-ol / 82 °C View Scheme

1: NaNH2 2: LiAlH4 View Scheme

1.1: 95 percent / K2CO3 / dimethylformamide / 10 h / 85 °C 2.1: 95 percent / aq. H2SO4; HNO3; AcOH / 50 h / 20 °C 3.1: 75 percent / sodium dithionite / H2O / 20 - 50 °C 4.1: 38 percent / KOH / 2-methyl-butan-2-ol / 82 °C 5.1: formamide / 20 - 100 °C 5.2: 78 percent / 7 h / 100 °C 6.1: 90 percent / POCl3; triethylamine / toluene / 24 h / 58 °C 7.1: 91 percent / triethylamine / propan-2-ol / 288 h / Heating 8.1: 54 percent / LiCl / dimethylformamide / 15 h / Heating View Scheme

1: 95 percent / K2CO3 / dimethylformamide / 10 h / 85 °C 2: 95 percent / aq. H2SO4; HNO3; AcOH / 50 h / 20 °C 3: 75 percent / sodium dithionite / H2O / 20 - 50 °C View Scheme

1: 391.5 g / potassium carbonate / dimethylformamide / 3 h / 100 °C 2: 391 g / hydroxylamine hydrochloride; pyridine / methanol / 1 h / Heating 3: 349 g / acetic anhydride / 3 h / 110 °C 4: 329 g / aq. nitric acid / acetic acid / 8 h / 45 - 50 °C View Scheme

toluene Erhitzen des Reaktionsprodukts mit wss. HCl;