Multi-step reaction with 6 steps
1: 63 percent / POCl3 / 1) 0 deg C, 20 min, 2) 65 deg C, 10 h
2: 79 percent / NaOH / H2O; dioxane / 2 h / 80 °C
3: 1) CuSO4*H2O, NH4OH, NH2OH*HCl, 2) pyridine / 1) THF, EtOH, 2) 115 deg C, 20 h
4: 92 percent / H2 / 5percent Pd-C / tetrahydrofuran / 10 h / Ambient temperature
5: 1) KCl, HCl(g) / 1) Et2O, 0 deg C, 2) GH2O, EtOH, 50 deg C, 30 min
6: 87 percent / H2, conc. HCl / 5percent Pd-C / tetrahydrofuran
With
pyridine; hydrogenchloride; ammonium hydroxide; sodium hydroxide; potassium chloride; hydroxylamine hydrochloride; hydrogen; copper(II) sulfate; trichlorophosphate;
palladium on activated charcoal;
In
tetrahydrofuran; 1,4-dioxane; water;
DOI:10.1021/jo00052a046