hydrogenchloride in diethyl ether

triethylamine; magnesium chloride in ethyl acetate

ammonia in tetrahydrofuran T=-50 - 20°C; 1.16667 h;

1: 4.30 g / CH2Cl2 / 48 h / 20 °C 2: thionyl chloride / CHCl3 / 20 °C 3: 2.56 g / sodium hydroxide / H2O / 20 °C / pH 8 View Scheme

in dichloromethane T=20°C; 48 h;

1.1: magnesium chloride / ethyl acetate / 0.5 h / 20 °C / |Inert atmosphere 1.2: 0.5 h / 20 °C / |Inert atmosphere 1.3: 2 h / |Inert atmosphere; |Reflux 2.1: potassium hydroxide; tetrabutylammomium bromide / N,N-dimethyl-formamide / 0.5 h / 20 °C / |Inert atmosphere 2.2: 16 h / 0 - 20 °C / |Inert atmosphere 2.3: 3 h / |Inert atmosphere 3.1: potassium tert-butylate / toluene / 16 h / |Inert atmosphere; |Reflux 4.1: Oxonereg; / water; methanol / 3 h / 55 - 60 °C 5.1: sodium hydrogen sulfide hydrate / N,N-dimethyl-formamide / 5 h / 20 °C / |Inert atmosphere 5.2: pH Ca. 1 - 2 6.1: potassium phosphate; hydroxylamine-o-sulphonic acid / water; tetrahydrofuran / 0 - 20 °C View Scheme

1.1: magnesium chloride / ethyl acetate / 0.5 h / 20 °C / |Inert atmosphere 1.2: 0.5 h / 20 °C / |Inert atmosphere 1.3: 2 h / |Inert atmosphere; |Reflux 2.1: potassium hydroxide; tetrabutylammomium bromide / N,N-dimethyl-formamide / 0.5 h / 20 °C / |Inert atmosphere 2.2: 16 h / 0 - 20 °C / |Inert atmosphere 2.3: 3 h / |Inert atmosphere 3.1: potassium tert-butylate / toluene / 16 h / |Inert atmosphere; |Reflux 4.1: Oxonereg; / water; methanol / 3 h / 55 - 60 °C 5.1: sodium hydrogen sulfide hydrate / N,N-dimethyl-formamide / 5 h / 20 °C / |Inert atmosphere 5.2: pH Ca. 1 - 2 6.1: potassium phosphate; hydroxylamine-o-sulphonic acid / water; tetrahydrofuran / 0 - 20 °C 7.1: N,N-dimethyl acetamide / 18 h / 90 °C / |Inert atmosphere 8.1: dichloromethane / 4 h / 20 °C / |Inert atmosphere 9.1: tert.-butylnitrite; copper(ll) bromide / acetonitrile / 0.17 h / 67 °C / |Inert atmosphere View Scheme