hydroxylamine hydrochloride; methylamine; copper(l) chloride 1.) methanol, 2.) methanol, 4 h; Multistep reaction. Yields of byproduct given;

1: PCl5 / benzene / Heating 2: 50 °C View Scheme

potassium hydroxide; potassium hypobromide in water T=-5°C; 2.5 h;

(i) NaNH2, liq. NH3, (ii) aq. NaOH, NaOBr; Multistep reaction;

1: 41.9 percent / ethylamine/CuCl, NH2OH*HCl / methanol / 3 h / 10 °C 2: 93.6 percent / H2 / Pt / methanol / 0 °C / 750.06 Torr 3: 100 percent / p-toluenesulphonic acid monohydrate / tetrahydrofuran; acetic acid; H2O / 7 h / Heating 4: 82.1 percent / 48percent HBr / acetic acid / 28 h / 122 - 123 °C 5: 51.2 percent / BuLi / hexamethylphosphoric acid triamide / 20 h / 0 °C 6: 95 percent / p-toluenesulphonic acid monohydrate / tetrahydrofuran; acetic acid; H2O / 6 h / Heating 7: H2, quinoline / Lindlar's catalyst / ethyl acetate / 37 °C View Scheme

1: 41.9 percent / ethylamine/CuCl, NH2OH*HCl / methanol / 3 h / 10 °C 2: 93.6 percent / H2 / Pt / methanol / 0 °C / 750.06 Torr 3: 100 percent / p-toluenesulphonic acid monohydrate / tetrahydrofuran; acetic acid; H2O / 7 h / Heating View Scheme