toluene-4-sulfonic acid in benzene 5 h; Heating;

1: indole-2,3-dione With sodium hydride in N,N-dimethyl-formamide T=0°C; 0.166667 h; 2: 2-bromo-1-ethanol in N,N-dimethyl-formamide T=20 - 70°C; 1.25 h;

potassium carbonate in acetonitrile T=20°C;

1: sodium sulfate; hydrogenchloride; hydroxylamine hydrochloride / water / 2 h / 85 °C 2: sulfuric acid / 0.5 h / 60 - 90 °C 3: toluene-4-sulfonic acid / toluene / 5 h / 130 °C View Scheme

1: sulfuric acid / 0.5 h / 60 - 90 °C 2: toluene-4-sulfonic acid / toluene / 5 h / 130 °C View Scheme

1: benzyltrimethylammonium hydroxide / ethanol / Heating 2: H2, NH3, Raney nickel / ethanol / 2 h / 50 °C / 3040 - 3800 Torr 3: conc. H2SO4 / 1 h / Ambient temperature 4: 71 percent / diethyl ether; 1,2-dichloro-ethane / 1 h View Scheme