hydroxylamine hydrochloride; sodium formate in formic acid Substitution; 3 h; Heating;

1: 5.75 g / AlCl3 / toluene / 3 h / 20 °C 2: 83 percent / NBS; AIBN / acetonitrile / 5 h / Heating 3: 81 percent / NaOAc / dimethylformamide / 8 h / Heating 4: 85 percent / sodium formate; NH2OH*HCl / formic acid / 3 h / Heating View Scheme

1: SOCl2 / 1 h / Heating 2: 5.75 g / AlCl3 / toluene / 3 h / 20 °C 3: 83 percent / NBS; AIBN / acetonitrile / 5 h / Heating 4: 81 percent / NaOAc / dimethylformamide / 8 h / Heating 5: 85 percent / sodium formate; NH2OH*HCl / formic acid / 3 h / Heating View Scheme

1: 83 percent / NBS; AIBN / acetonitrile / 5 h / Heating 2: 81 percent / NaOAc / dimethylformamide / 8 h / Heating 3: 85 percent / sodium formate; NH2OH*HCl / formic acid / 3 h / Heating View Scheme

1: 81 percent / NaOAc / dimethylformamide / 8 h / Heating 2: 85 percent / sodium formate; NH2OH*HCl / formic acid / 3 h / Heating View Scheme

1: 91 percent / PPh3; Et3N; Pd(OAc)2 / 5 h / Heating 2: 92 percent / TBAF; AcOH / tetrahydrofuran / 2 h / 20 °C View Scheme