Multi-step reaction with 8 steps
1: 1.) NaH / 1.) DMF, rt, 1 h, 2.) benzene, rt, 1 h
2: 1.) NaH / 1.) DMSO, benzene, 60 deg C, 20 min, 2.) 60 deg C, 1 h
3: 94 percent / AcOH, 10percent H2SO4 / 0.17 h / 60 °C
4: 94 percent / pyridine / 1.) 10 deg C to rt, 2.) 30 deg C, 1 h
5: 98 percent / H2 / 10percent Pd-C / methanol; benzene / 3 h / 2325.2 - 2850.2 Torr
6: 1.) aq. NaNO2, conc. HCl, 2.) Cu2O / 1.) acetone, 0 deg C, 2.) 40 to 43 deg C, 30 min
7: 2.) AcOH, conc. HCl / 1.) sulfolane, 115 to 120 deg C, 80 min, 2.) H2O, 85 to 90 deg c, 12 h
8: 56 percent
With
pyridine; copper(I) oxide; hydrogenchloride; sulfuric acid; hydrogen; sodium hydride; acetic acid; sodium nitrite;
palladium on activated charcoal;
In
methanol; benzene;
DOI:10.1021/jm00122a022