hydrogenchloride; sodium chloride in ethanol; chloroform; acetone

hydrogenchloride in ethanol 17 h; Heating;

hydrogenchloride; sodium hydroxide in methanol 1.) 55 deg C, 16 h; 2.) iso-PrOH, acetone, 0-5 deg C, 15 min.;

1: 95 percent / H2 / 10percent Pd-C / methanol / Ambient temperature 2: 96.4 percent / Et3N / CH2Cl2 / 10 h / Ambient temperature 3: 70 percent / pyridine / CH2Cl2 / 15 h / Ambient temperature 4: 73.5 percent / dimethylformamide / 17 h / 100 - 105 °C 5: 77.7 percent / LiAlH4 / tetrahydrofuran / 3 h / Ambient temperature 6: 73.4 percent / 0.5 N HCl / ethanol / 17 h / Heating View Scheme

1: 77.7 percent / LiAlH4 / tetrahydrofuran / 3 h / Ambient temperature 2: 73.4 percent / 0.5 N HCl / ethanol / 17 h / Heating View Scheme

1: 96.4 percent / Et3N / CH2Cl2 / 10 h / Ambient temperature 2: 70 percent / pyridine / CH2Cl2 / 15 h / Ambient temperature 3: 73.5 percent / dimethylformamide / 17 h / 100 - 105 °C 4: 77.7 percent / LiAlH4 / tetrahydrofuran / 3 h / Ambient temperature 5: 73.4 percent / 0.5 N HCl / ethanol / 17 h / Heating View Scheme

1: 70 percent / pyridine / CH2Cl2 / 15 h / Ambient temperature 2: 73.5 percent / dimethylformamide / 17 h / 100 - 105 °C 3: 77.7 percent / LiAlH4 / tetrahydrofuran / 3 h / Ambient temperature 4: 73.4 percent / 0.5 N HCl / ethanol / 17 h / Heating View Scheme

1: 73.5 percent / dimethylformamide / 17 h / 100 - 105 °C 2: 77.7 percent / LiAlH4 / tetrahydrofuran / 3 h / Ambient temperature 3: 73.4 percent / 0.5 N HCl / ethanol / 17 h / Heating View Scheme

Yield given;