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. 4: 95 percent / 12 N HCl / 0 °C View Scheme

hydroxylamine; potassium carbonate in dichloromethane; water 2.5 h; Heating;

1: K2CO3 / H2O; CH2Cl2 / 2 h / Ambient temperature 2: NH2OH*HCl, K2CO3 / H2O; methanol / 2 h / Heating View Scheme

acetic acid; sodium nitrite in water T=0°C; 24 h;

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