1: 4-(methylamino)-3-nitrobenzoic acid With thionyl chloride in N,N-dimethyl-formamide T=25 - 80°C; 1.25 h; 2: 3-(pyridin-2-ylamino)propionic acid ethyl ester With triethylamine in ethyl acetate; N,N-dimethyl-formamide 1 h;

triethylamine in tetrahydrofuran T=20°C;

1: SOCl2 / dimethylformamide / 0.5 h / Heating 2: Et3N / tetrahydrofuran / 20 °C View Scheme

1.1: 25 - 55 °C 2.1: thionyl chloride / N,N-dimethyl-formamide / 1.25 h / 25 - 80 °C 2.2: 1 h View Scheme

1.1: palladium on activated charcoal / ethyl acetate / 0.33 h / 25 - 55 °C / |High pressure 2.1: 1,1'-carbonyldiimidazole / toluene / 2 h / 55 - 60 °C 2.2: 6 h / 60 - 100 °C 3.1: hydrogenchloride / ethanol / 25 - 35 °C 4.1: potassium carbonate / water; acetone / 1 h / 10 °C 5.1: acetone / 2 h / 25 - 30 °C View Scheme

hydrogen; palladium 10 on activated carbon in ethyl acetate T=50°C; P=2250.23 - 3000.3 Torr; 4 - 5 h; Product distribution / selectivity;

1.1: 65 percent / H2 / 10percent Pd/C / methanol / 20 °C 2.1: CDI / tetrahydrofuran / 50 °C 2.2: tetrahydrofuran / 24 h / Heating 3.1: glacial acetic acid / 1 h / Heating View Scheme