hydrogenchloride in ethanol T=10 - 65°C; 4.25 h; Product distribution / selectivity;

1: With sodium acetate in ethanol 3 h; Heating / reflux; 2: With hydrogenchloride in ethanol; water 18 h; Heating / reflux; 3: With ammonia in ethanol; water T=20°C;

1: 2N HCl / 6 h / Heating 2: 12.2 g / 11percent ethanolic HCl / 1 h / Ambient temperature View Scheme

1: 63 percent / NaH / dimethylformamide 2: H2 / 10percent Pd-C / methanol / 760 Torr / Ambient temperature 3: 1.)47percent HBr, NaNO2, 2.)Cu2O / 1.)MeOH, H2O, 5 deg C, 20 min., 2.)40 deg C 4: 53 percent / NaOAc / ethanol / Heating 5: 2N HCl / 6 h / Heating 6: 12.2 g / 11percent ethanolic HCl / 1 h / Ambient temperature View Scheme

1: With hydrogenchloride; water 8 h; Heating / reflux; 2: With hydrogenchloride in ethyl acetate T=25 - 30°C; 2 h; Product distribution / selectivity;

1: With sodium tetrahydroborate; Co(NO3)2⋅6H2O; dmgH2; sodium hydroxide in water; N,N-dimethyl-formamide T=35°C; 6 h; Large scale reaction; 2: With acetic acid in water; N,N-dimethyl-formamide T=25°C; pH=6.5 - 7; 0.75 h; Large scale reaction; 3: With hydrogenchloride in water; isopropyl alcohol T=25 - 80°C; Large scale reaction;

1: H2 / 10percent Pd-C / methanol / 760 Torr / Ambient temperature 2: 1.)47percent HBr, NaNO2, 2.)Cu2O / 1.)MeOH, H2O, 5 deg C, 20 min., 2.)40 deg C 3: 53 percent / NaOAc / ethanol / Heating 4: 2N HCl / 6 h / Heating 5: 12.2 g / 11percent ethanolic HCl / 1 h / Ambient temperature View Scheme

1: 63 percent / NaH / dimethylformamide 2: H2 / 10percent Pd-C / methanol / 760 Torr / Ambient temperature 3: 1.)47percent HBr, NaNO2, 2.)Cu2O / 1.)MeOH, H2O, 5 deg C, 20 min., 2.)40 deg C 4: 53 percent / NaOAc / ethanol / Heating 5: 2N HCl / 6 h / Heating 6: 12.2 g / 11percent ethanolic HCl / 1 h / Ambient temperature View Scheme

1: 0.5 h / 120 °C 2: sodium hydroxide / water / 2 h / 40 °C 3: thionyl chloride; triethylamine / dichloromethane / 1.25 h / 0 - 5 °C 4: N,N-dimethyl-formamide / 14 h / 80 °C 5: pyrrolidine / methanol / 2 h / 50 - 55 °C / |Large scale 6: sodium tetrahydroborate; dmgH2; CoCl2.6H2O / water; N,N-dimethyl-formamide / 4 h / 65 - 85 °C / |Large scale 7: thionyl chloride / chloroform / 2 h / |Reflux 8: hydrogenchloride 9: zinc; propionic acid / ethanol / 12 h 10: hydrogenchloride / water; ethanol View Scheme

1.1: N-bromosuccinmide / tert-butyl alcohol; water / 1.5 h / 25 °C / |Large scale 1.2: 0.75 h / |Large scale 1.3: PEG 4000 / 17 h / 78 °C / |Large scale 2.1: thionyl chloride / chloroform / 1 h / |Reflux 3.1: acetic acid; piperidine / toluene / |Heating 4.1: hydrogen / tetrahydrofuran / 12 h 5.1: hydrogenchloride / water; ethanol View Scheme