toluene-4-sulfonic acid; sodium hydrogensulfite in isobutyramide T=115°C;

iodine; potassium carbonate in N,N-dimethyl-formamide T=70°C; 17 h; Product distribution / selectivity;

1: With 4-methyl-morpholine; benzotriazol-1-ol; N'-(3-dimethylaminopropyl)-N-ethylcarbodiimide in tetrahydrofuran T=20°C; 3 h; 2: With ammonia in tetrahydrofuran; water T=20°C; 16 h;

ammonium hydroxide in diethyl ether

1: With dihydrogen peroxide; sodium hydroxide in tetrahydrofuran; water T=70°C; 2: With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride in tetrahydrofuran T=20°C; 3 h; 3: With ammonia in tetrahydrofuran; water T=20°C; 16 h;

1.1: hydrogenchloride / diethyl ether / 1.5 h / 0 - 10 °C 2.1: diethyl ether / 2 h / 170 °C 3.1: sodium hydroxide; dihydrogen peroxide / tetrahydrofuran; water / 70 °C 3.2: 3 h / 20 °C 3.3: 16 h / 20 °C View Scheme

1.1: diethyl ether / 2 h / 170 °C 2.1: sodium hydroxide; dihydrogen peroxide / tetrahydrofuran; water / 70 °C 2.2: 3 h / 20 °C 2.3: 16 h / 20 °C View Scheme