thionyl chloride in tetrahydrofuran; water; triethylamine; N,N-dimethyl-formamide

1: 3,4-dinitrobenzoic acid With thionyl chloride; N,N-dimethyl-formamide in tetrahydrofuran T=65 - 70°C; 2.5 - 3 h; Heating / reflux; 2: morpholine With triethylamine in tetrahydrofuran T=0 - 20°C; Product distribution / selectivity;

triethylamine in tetrahydrofuran T=0°C; 3 h;

1.1: thionyl chloride; N,N-dimethyl-formamide / tetrahydrofuran / 6 h / |Reflux 2.1: triethylamine / tetrahydrofuran / 2 h / 0 - 5 °C 2.2: 10 - 20 °C View Scheme

hydrogen; palladium 10 on activated carbon in methanol T=20°C; 10 h;

1.1: sodium tetrahydroborate; boron trifluoride diethyl etherate / tetrahydrofuran / 0 - 20 °C / |Inert atmosphere 1.2: 0 °C / |Reflux 2.1: 5 palladium on charcoal; hydrogen / ethanol / 48 h / 20 °C View Scheme

1: With sodium tetrahydroborate; boron trifluoride diethyl etherate in tetrahydrofuran T=0 - 20°C; 3 h; 2: With methanol in tetrahydrofuran T=0 - 20°C; 1 h; Heating / reflux; Product distribution / selectivity;

1.1: sodium tetrahydroborate; boron trifluoride diethyl etherate / tetrahydrofuran / 0 - 20 °C / |Inert atmosphere 1.2: 0 °C / |Reflux 2.1: 5 palladium on charcoal; hydrogen / ethanol / 48 h / 20 °C 3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 24 h / 20 °C 3.2: 3 h / |Reflux View Scheme

1.1: sodium tetrahydroborate; boron trifluoride diethyl etherate / tetrahydrofuran / 0 - 20 °C / |Inert atmosphere 1.2: 0 °C / |Reflux 2.1: 5 palladium on charcoal; hydrogen / ethanol / 48 h / 20 °C 3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 24 h / 20 °C 3.2: 3 h / |Reflux 4.1: 5 palladium on charcoal; hydrogen / ethanol / 48 h / 20 °C View Scheme