hydrogenchloride; sodium nitrite in water T=0°C;

1: 91.5 percent / aq. sodium thiosulfate, NaOH / 1 h / 30 °C 2: 65 percent / 50percent aq. NaOH / triethylbenzylammonium chloride / acetonitrile / 5 h / Ambient temperature View Scheme

hydrogenchloride 1.) from 50 to 60 deg C, 2 h, 2.) RT, 16 h; Yield given. Multistep reaction;