in 12N-hydrochloric acid

hydrogenchloride T=0°C;

in sodium borohydride; ethanol; dichloromethane; water; acetone

1: 84 percent / NH2OH, K2CO3 / H2O; CH2Cl2 / 2.5 h / Heating 2: 83 percent / NaNO2, CH3COOH / H2O / 24 h / 0 °C 3: 1.) CH3ONa / 1.) DMF, RT, 1 h, 2.) DMF, 80 deg C, 5 h 4: 1.) CuCl2*2H2O, 2.) NaBH4 / 1.) ethanol, 0 deg C, 1 h, 2.) ethanol, 0 deg C 45 min. View Scheme

1: 83 percent / NaNO2, CH3COOH / H2O / 24 h / 0 °C 2: 1.) CH3ONa / 1.) DMF, RT, 1 h, 2.) DMF, 80 deg C, 5 h 3: 1.) CuCl2*2H2O, 2.) NaBH4 / 1.) ethanol, 0 deg C, 1 h, 2.) ethanol, 0 deg C 45 min. View Scheme

1: 85 percent / K2CO3 / H2O; CH2Cl2 / 2 h / Ambient temperature 2: 84 percent / NH2OH, K2CO3 / H2O; CH2Cl2 / 2.5 h / Heating 3: 83 percent / NaNO2, CH3COOH / H2O / 24 h / 0 °C 4: 1.) CH3ONa / 1.) DMF, RT, 1 h, 2.) DMF, 80 deg C, 5 h 5: 1.) CuCl2*2H2O, 2.) NaBH4 / 1.) ethanol, 0 deg C, 1 h, 2.) ethanol, 0 deg C 45 min. View Scheme

sodium tetrahydroborate 1.) ethanol, 0 deg C, 1 h, 2.) ethanol, 0 deg C 45 min.; Yield given. Multistep reaction;

1: 1.) CH3ONa / 1.) DMF, RT, 1 h, 2.) DMF, 80 deg C, 5 h 2: 1.) CuCl2*2H2O, 2.) NaBH4 / 1.) ethanol, 0 deg C, 1 h, 2.) ethanol, 0 deg C 45 min. View Scheme

1: 1.) CH3ONa / 1.) DMF, RT, 1 h, 2.) DMF, 80 deg C, 5 h 2: 1.) CuCl2*2H2O, 2.) NaBH4 / 1.) ethanol, 0 deg C, 1 h, 2.) ethanol, 0 deg C 45 min. View Scheme