1: With hydrogen; acetic acid; platinum(IV) oxide in methanol T=50 - 60°C; P=3677.86 Torr; 2: With hydrogenchloride in ethanol; isopropyl alcohol 1 h; Reflux; Product distribution / selectivity;

hydrogenchloride in ethanol T=0 - 30°C; pH=1.0 - 1.5; 1 h; Product distribution / selectivity;

in hydrogenchloride; methanesulfonic acid; water

in methanol; water; ethyl acetate; N,N-dimethyl-formamide

hydrogenchloride in ethyl acetate; N,N-dimethyl-formamide

1.1: sodium hydrogencarbonate; iodine / dichloromethane / 25 - 30 °C 2.1: dichloromethane / 1.5 h / 25 °C 3.1: copper(l) iodide; lithium chloride / N,N-dimethyl-formamide / 0.5 h / 25 °C 3.2: 25 °C 4.1: potassium hydroxide; ethanol / 15 - 25 °C 5.1: potassium tert-butylate / 1-methyl-pyrrolidin-2-one / 80 - 85 °C 5.2: 0.5 h / 25 °C 6.1: trifluoroacetic acid / ethanol / 25 °C / Reflux 6.2: 10 - 15 °C / pH 8 7.1: hydrogen; acetic acid / palladium 10 on activated carbon / 25 °C / 1448.05 - 2172.08 Torr 7.2: 10 °C / pH 7.5 - 8.5 8.1: hydrogenchloride / isopropyl alcohol; acetone / 5 - 10 °C / pH 1 View Scheme

1.1: dichloromethane / 1.5 h / 25 °C 2.1: copper(l) iodide; lithium chloride / N,N-dimethyl-formamide / 0.5 h / 25 °C 2.2: 25 °C 3.1: potassium hydroxide; ethanol / 15 - 25 °C 4.1: potassium tert-butylate / 1-methyl-pyrrolidin-2-one / 80 - 85 °C 4.2: 0.5 h / 25 °C 5.1: trifluoroacetic acid / ethanol / 25 °C / Reflux 5.2: 10 - 15 °C / pH 8 6.1: hydrogen; acetic acid / palladium 10 on activated carbon / 25 °C / 1448.05 - 2172.08 Torr 6.2: 10 °C / pH 7.5 - 8.5 7.1: hydrogenchloride / isopropyl alcohol; acetone / 5 - 10 °C / pH 1 View Scheme

1.1: copper(l) iodide; lithium chloride / N,N-dimethyl-formamide / 0.5 h / 25 °C 1.2: 25 °C 2.1: potassium hydroxide; ethanol / 15 - 25 °C 3.1: potassium tert-butylate / 1-methyl-pyrrolidin-2-one / 80 - 85 °C 3.2: 0.5 h / 25 °C 4.1: trifluoroacetic acid / ethanol / 25 °C / Reflux 4.2: 10 - 15 °C / pH 8 5.1: hydrogen; acetic acid / palladium 10 on activated carbon / 25 °C / 1448.05 - 2172.08 Torr 5.2: 10 °C / pH 7.5 - 8.5 6.1: hydrogenchloride / isopropyl alcohol; acetone / 5 - 10 °C / pH 1 View Scheme

1.1: copper(l) iodide; lithium chloride / N,N-dimethyl-formamide / 0.5 h / 25 °C 1.2: 25 °C 2.1: potassium hydroxide; ethanol / 15 - 25 °C 3.1: potassium tert-butylate / 1-methyl-pyrrolidin-2-one / 80 - 85 °C 4.1: potassium hydroxide / methanol / 8 h / 60 - 65 °C 5.1: trifluoroacetic acid / dichloromethane / 0.17 h / 25 °C 5.2: 25 - 30 °C 5.3: 10 - 15 °C 6.1: hydrogen; acetic acid / palladium 10 on activated carbon / 25 °C / 724.03 Torr 6.2: 10 °C / pH 7.5 - 8.5 7.1: hydrogenchloride / isopropyl alcohol; acetone / 5 - 10 °C / pH 1 View Scheme

1.1: potassium hydroxide; ethanol / 15 - 25 °C 2.1: potassium tert-butylate / 1-methyl-pyrrolidin-2-one / 80 - 85 °C 2.2: 0.5 h / 25 °C 3.1: trifluoroacetic acid / ethanol / 25 °C / Reflux 3.2: 10 - 15 °C / pH 8 4.1: hydrogen; acetic acid / palladium 10 on activated carbon / 25 °C / 1448.05 - 2172.08 Torr 4.2: 10 °C / pH 7.5 - 8.5 5.1: hydrogenchloride / isopropyl alcohol; acetone / 5 - 10 °C / pH 1 View Scheme