hydrogenchloride; ammonium chloride; sodium amide 1.) liquid ammonia, -78 deg C, 20 h; 2.) ether;

1: 98 percent / N-bromosuccinimide / CH2Cl2 / 24 h / Ambient temperature 2: 95 percent / LiAlH4 / tetrahydrofuran / 1 h / Ambient temperature 3: 96 percent / POCl3, pyridine / toluene / 2 h / Ambient temperature 4: 65 percent / 1.) sodium amide, NH4Cl; 2.) gaseous hydrochlorid acid / 1.) liquid ammonia, -78 deg C, 20 h; 2.) ether View Scheme

1: 95 percent / LiAlH4 / tetrahydrofuran / 1 h / Ambient temperature 2: 96 percent / POCl3, pyridine / toluene / 2 h / Ambient temperature 3: 65 percent / 1.) sodium amide, NH4Cl; 2.) gaseous hydrochlorid acid / 1.) liquid ammonia, -78 deg C, 20 h; 2.) ether View Scheme

1: 96 percent / POCl3, pyridine / toluene / 2 h / Ambient temperature 2: 65 percent / 1.) sodium amide, NH4Cl; 2.) gaseous hydrochlorid acid / 1.) liquid ammonia, -78 deg C, 20 h; 2.) ether View Scheme