Multi-step reaction with 13 steps
1: 45.3 percent / NaOEt / ethanol / 2 h / 60 °C
2: 1.) NaNO2, HCl, 2.) HCl, H2O / 1.) water, 2.5 h, 2.) 1 h
3: 100 percent / SOCl2 / CHCl3; dimethylformamide / Heating
4: 81 percent / MgO, H2 / 10percent Pd/C / dioxane / 2585.7 Torr
5: 89 percent / H2 / Raney Ni / acetic acid / 2585.7 Torr
6: 95 percent / NaNO2, AcOH, Ac2O / 2 h / Ambient temperature
7: 91 percent / Heating
8: 87 percent / BCl3 / CH2Cl2 / a) -78 deg C, 3 h, b) RT, overnight
9: 93 percent / pyridine / 48 h / Ambient temperature
10: p-TsOH, hexamethyldisilazane, NH3 / 120 h / 155 - 160 °C
11: 50percent aq. MeOH / 4 h / Heating
12: 100 percent / HBr / dioxane / 20 h
13: 93 percent / N,N-dimethyl-acetamide / 72 h / Ambient temperature
With
pyridine; hydrogenchloride; methanol; thionyl chloride; ammonia; water; hydrogen bromide; hydrogen; sodium ethanolate; acetic anhydride; magnesium oxide; boron trichloride; toluene-4-sulfonic acid; acetic acid; 1,1,1,3,3,3-hexamethyl-disilazane; sodium nitrite;
palladium on activated charcoal; nickel;
In
1,4-dioxane; ethanol; dichloromethane; chloroform; N,N-dimethyl acetamide; acetic acid; N,N-dimethyl-formamide;
DOI:10.1021/jm00155a021