copper diacetate; water; oxygen; palladium dichloride in N,N-dimethyl acetamide T=23°C;

formic acid; hydroxylamine hydrochloride 0.5 h; Heating / reflux;

1: 97 percent / MgSO4 / CH2Cl2 / Ambient temperature 2: 89 percent / t-BuOK / tetrahydrofuran / 1 h / Heating 3: 1.) aq. oxalic acid, 2.) aq. NaOH / 1.) CH2Cl2, reflux, 2 h, 2.) 0 deg C View Scheme