1: With potassium tert-butylate in tetrahydrofuran T=-50 - 20°C; 1 h; 2: With water in tetrahydrofuran T=20°C; 3 h; 3: With hydrogenchloride T=90°C; pH=0.5; Further stages.;

5-methylquinoline; sulfuric acid; nitric acid 0.0833333 h; Ambient temperature;

diarsenic pentoxide; sulfuric acid

1: 99 percent / dimethylformamide / 16 h / 140 °C 2: 88 percent / sodium periodate / tetrahydrofuran; H2O / 2 h / 25 °C 3: 84 percent / Fe powder, conc. HCl / ethanol; acetic acid; H2O / 1) reflux, 15 min; 2) 25 deg C, 25 min 4: 45 percent / KOH / ethanol / 15 h / Heating View Scheme

hydrogen; palladium in methanol T=20°C;

1: dimethylformamide / 110 °C 2: Fe; AcOH / ethanol View Scheme

1: 99 percent / dimethylformamide / 16 h / 140 °C 2: 88 percent / sodium periodate / tetrahydrofuran; H2O / 2 h / 25 °C View Scheme

1: 99 percent / dimethylformamide / 16 h / 140 °C 2: 88 percent / sodium periodate / tetrahydrofuran; H2O / 2 h / 25 °C 3: 84 percent / Fe powder, conc. HCl / ethanol; acetic acid; H2O / 1) reflux, 15 min; 2) 25 deg C, 25 min View Scheme