1: With hydrogenchloride in methanol; water T=50°C; 1 h; 2: With ammonia in water

1: N,N-dimethyl-formamide; thionyl chloride / dichloromethane / 2.5 h / Reflux 2: triethylamine / dichloromethane / 0 °C 3: sodium tetrahydroborate / NiII chloride hexahydrate / methanol / 5 - 23 °C 4: hydrogenchloride; benzotriazol-1-ol / 1-methyl-pyrrolidin-2-one / 4 h / 120 °C / Inert atmosphere 5: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 5 - 20 °C 6: ammonium hydroxide; p-toluenesulfonyl chloride / dichloromethane / 0 - 20 °C 7: hydrogenchloride / water; methanol / 1 h / 50 °C View Scheme

1: nitric acid / propionic acid / 3.67 h / Reflux 2: N,N-dimethyl-formamide; thionyl chloride / dichloromethane / 2.5 h / Reflux 3: triethylamine / dichloromethane / 0 °C 4: sodium tetrahydroborate / NiII chloride hexahydrate / methanol / 5 - 23 °C 5: hydrogenchloride; benzotriazol-1-ol / 1-methyl-pyrrolidin-2-one / 4 h / 120 °C / Inert atmosphere 6: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 5 - 20 °C 7: ammonium hydroxide; p-toluenesulfonyl chloride / dichloromethane / 0 - 20 °C 8: hydrogenchloride / water; methanol / 1 h / 50 °C View Scheme

1: triethylamine / dichloromethane / 0 °C 2: sodium tetrahydroborate / NiII chloride hexahydrate / methanol / 5 - 23 °C 3: hydrogenchloride; benzotriazol-1-ol / 1-methyl-pyrrolidin-2-one / 4 h / 120 °C / Inert atmosphere 4: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 5 - 20 °C 5: ammonium hydroxide; p-toluenesulfonyl chloride / dichloromethane / 0 - 20 °C 6: hydrogenchloride / water; methanol / 1 h / 50 °C View Scheme

1: sodium tetrahydroborate / NiII chloride hexahydrate / methanol / 5 - 23 °C 2: hydrogenchloride; benzotriazol-1-ol / 1-methyl-pyrrolidin-2-one / 4 h / 120 °C / Inert atmosphere 3: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 5 - 20 °C 4: ammonium hydroxide; p-toluenesulfonyl chloride / dichloromethane / 0 - 20 °C 5: hydrogenchloride / water; methanol / 1 h / 50 °C View Scheme

1: ammonium hydroxide; p-toluenesulfonyl chloride / dichloromethane / 0 - 20 °C 2: hydrogenchloride / water; methanol / 1 h / 50 °C View Scheme

1: hydrogenchloride; benzotriazol-1-ol / 1-methyl-pyrrolidin-2-one / 4 h / 120 °C / Inert atmosphere 2: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 5 - 20 °C 3: ammonium hydroxide; p-toluenesulfonyl chloride / dichloromethane / 0 - 20 °C 4: hydrogenchloride / water; methanol / 1 h / 50 °C View Scheme

1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 5 - 20 °C 2: ammonium hydroxide; p-toluenesulfonyl chloride / dichloromethane / 0 - 20 °C 3: hydrogenchloride / water; methanol / 1 h / 50 °C View Scheme

1.1: 3-chloro-benzenecarboperoxoic acid / chloroform / |Reflux 2.1: hydrazine hydrate / ethanol / 90 °C 2.2: 2 h / 20 - 90 °C View Scheme