phosphoric acid; sulfuric acid; sodium nitrite T=0°C; 4 h;

zinc cyanide in N,N-dimethyl-formamide T=110°C; 3 h; Yield given;

1: 20 percent NaCl-solution / pH </= 1 2: NaHCO3 / H2O / 8 h / 15 - 25 °C 3: 1) NaNO2, conc. H2SO4; 2) amidosulfuric acid, HCl / 1) 2 h, r.t.; 2) water, 6 h 4: Zn(CN)2 / dimethylformamide / 3 h / 110 °C View Scheme

1: HCl / H2O / 8 h / pH = 1,5-3,5 2: 20 percent NaCl-solution / pH </= 1 3: NaHCO3 / H2O / 8 h / 15 - 25 °C 4: 1) NaNO2, conc. H2SO4; 2) amidosulfuric acid, HCl / 1) 2 h, r.t.; 2) water, 6 h 5: Zn(CN)2 / dimethylformamide / 3 h / 110 °C View Scheme

1: NaHCO3 / H2O / 8 h / 15 - 25 °C 2: 1) NaNO2, conc. H2SO4; 2) amidosulfuric acid, HCl / 1) 2 h, r.t.; 2) water, 6 h 3: Zn(CN)2 / dimethylformamide / 3 h / 110 °C View Scheme

1: conc. NH3-solution / dimethylformamide 2: 86 percent / POCl3 / dimethylformamide / 4 h / 40 - 45 °C 3: 80 percent / hydroxylamine hydrochloride, KOH / bis-(2-hydroxy-ethyl) ether; methanol / 2 h / 25 °C 4: 60 percent / 96 percent H2SO4, 85 percent H3PO4, conc. H2SO4, NaNO2 / 4 h / 0 °C View Scheme

1: SOCl2 / dimethylformamide / 6 h / Heating 2: conc. NH3-solution / dimethylformamide 3: 86 percent / POCl3 / dimethylformamide / 4 h / 40 - 45 °C 4: 80 percent / hydroxylamine hydrochloride, KOH / bis-(2-hydroxy-ethyl) ether; methanol / 2 h / 25 °C 5: 60 percent / 96 percent H2SO4, 85 percent H3PO4, conc. H2SO4, NaNO2 / 4 h / 0 °C View Scheme

1: 86 percent / POCl3 / dimethylformamide / 4 h / 40 - 45 °C 2: 80 percent / hydroxylamine hydrochloride, KOH / bis-(2-hydroxy-ethyl) ether; methanol / 2 h / 25 °C 3: 60 percent / 96 percent H2SO4, 85 percent H3PO4, conc. H2SO4, NaNO2 / 4 h / 0 °C View Scheme

1: 80 percent / hydroxylamine hydrochloride, KOH / bis-(2-hydroxy-ethyl) ether; methanol / 2 h / 25 °C 2: 60 percent / 96 percent H2SO4, 85 percent H3PO4, conc. H2SO4, NaNO2 / 4 h / 0 °C View Scheme

1: 1) NaNO2, conc. H2SO4; 2) amidosulfuric acid, HCl / 1) 2 h, r.t.; 2) water, 6 h 2: Zn(CN)2 / dimethylformamide / 3 h / 110 °C View Scheme