Multi-step reaction with 6 steps
1: 1.) NaH / 1.) DMF, 30 min, room temperature, 2.a) DMF, 30 min, room temperature, b.) 2 h, 90 deg C
2: 9.2 g / H2 / 10percent Pd-C / ethyl acetate / 4 h / Ambient temperature
3: 1.) 12 N HCl, NaNO2, 2.) Na2CO3 / 1.) H2O, 2-3 deg C, 20 min, 2.a) H2O, 1.5 h, 3 deg C, b.) 2 h, 50 deg C
4: 93 percent / H2S (g), NEt3 / dimethylformamide / 0.5 h / 90 °C
5: 100 percent / benzene / 3.25 h / Heating
6: 74 percent / 1 N aq. NaOH / ethanol / Heating
With
hydrogenchloride; sodium hydroxide; hydrogen sulfide; hydrogen; sodium hydride; sodium carbonate; triethylamine; sodium nitrite;
palladium on activated charcoal;
In
ethanol; ethyl acetate; N,N-dimethyl-formamide; benzene;
DOI:10.1248/cpb.39.2323