1: With formic acid; water; Raney nickel T=30 - 105°C; 4 h; 2: With ammonia; water in water T=5 - 10°C; pH=4.7 - 5;

tetra(n-butyl)ammonium hydrogensulfate; potassium hydroxide in water; toluene T=85°C; 0.333333 h; Sealed vesselMicrowave irradiation;

1: 2-[N-(2-hydroxyethyl)-N-methylamino]pyridine With potassium hydroxide in DMF (N,N-dimethyl-formamide) T=20°C; 2 h; 2: 4-fluorobenzaldehyde in DMF (N,N-dimethyl-formamide) T=20 - 40°C; 24 h;

polymer-supported chromic acid in tetrahydrofuran 48 h; Heating;

1: 63 percent / 15 h / 120 °C 2: 1.) NaH / 1.) DMF, RT, 2.) DMF, RT, 18 h View Scheme

1: 82 percent / 24 h / 120 °C 2: 86 percent / polymer-supported chromic acid / tetrahydrofuran / 48 h / Heating View Scheme

1.1: 96 percent / K2CO3 / dimethylformamide / 2 h / 90 °C 2.1: 100 percent / Amberlyst H-15 / tetrahydrofuran / 48 h / 20 °C 3.1: BH3*THF / tetrahydrofuran / 24 h / 65 °C 3.2: aq. HCl / tetrahydrofuran / 1 h / 20 °C 3.3: 84 percent / Et2NH / tetrahydrofuran / 16 h / 20 °C 4.1: 82 percent / 24 h / 120 °C 5.1: 86 percent / polymer-supported chromic acid / tetrahydrofuran / 48 h / Heating View Scheme

1.1: 100 percent / Amberlyst H-15 / tetrahydrofuran / 48 h / 20 °C 2.1: BH3*THF / tetrahydrofuran / 24 h / 65 °C 2.2: aq. HCl / tetrahydrofuran / 1 h / 20 °C 2.3: 84 percent / Et2NH / tetrahydrofuran / 16 h / 20 °C 3.1: 82 percent / 24 h / 120 °C 4.1: 86 percent / polymer-supported chromic acid / tetrahydrofuran / 48 h / Heating View Scheme

1: 82 percent / 24 h / 120 °C 2: 86 percent / polymer-supported chromic acid / tetrahydrofuran / 48 h / Heating View Scheme

1.1: BH3*THF / tetrahydrofuran / 24 h / 65 °C 1.2: aq. HCl / tetrahydrofuran / 1 h / 20 °C 1.3: 84 percent / Et2NH / tetrahydrofuran / 16 h / 20 °C 2.1: 82 percent / 24 h / 120 °C 3.1: 86 percent / polymer-supported chromic acid / tetrahydrofuran / 48 h / Heating View Scheme