Multi-step reaction with 7 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: 82 percent / LiAlH4 / tetrahydrofuran / 4 h / Ambient temperature
6: 64 percent / gl. HOAc, 85percent H3PO4 / 2 h / 100 °C
7: 66 percent / 1N NaOH / methanol / Ambient temperature
With
pyridine; ammonium hydroxide; sodium hydroxide; lithium aluminium tetrahydride; phosphoric acid; hydroxylamine hydrochloride; hydrogen; copper(II) sulfate; acetic acid; trichlorophosphate;
palladium on activated charcoal;
In
tetrahydrofuran; 1,4-dioxane; methanol; water;
DOI:10.1021/jo00052a046