Multi-step reaction with 20 steps
1: 1.) Na / 1.) ethanol; 2.) ethanol, reflux, 0.5 h
2: H2O, KOH / Heating
3: 94.7 percent / quinoline / 0.33 h / Heating
4: 89.4 percent / cc. H2SO4 / toluene
5: 89.6 percent / B2H6 / tetrahydrofuran
6: 91.2 percent / 48 percent HBr / H2O / 0.5 h / Heating
7: 1.) Na / 1.) ethanol; 2.) ethanol, reflux
8: H2O, KOH / Heating
9: 94.6 percent / quinoline / 0.33 h / Heating
10: SOCl2 / Heating
11: SnCl2 / CH2Cl2; nitromethane / 1 h / Ambient temperature
12: 88.3 percent / B2H6 / tetrahydrofuran
13: 98.1 percent / PhCH2ONa / Heating
14: H2, triethylamine / 10 percent Pd/C / tetrahydrofuran / Ambient temperature
15: dimethylformamide / Heating
16: POCl3 / CH2Cl2 / 0.5 h
17: NaHCO3 / H2O / Heating
18: cyclohexylamine / toluene / 2 h / Heating
19: SO2Cl2 / CH2Cl2 / Ambient temperature
20: glacial acetic acid / 1 h / 80 °C
With
quinoline; potassium hydroxide; thionyl chloride; sulfuryl dichloride; sulfuric acid; water; hydrogen bromide; hydrogen; sodium; sodium hydrogencarbonate; cyclohexylamine; acetic acid; triethylamine; sodium phenyl-methanolate; tin(ll) chloride; diborane; trichlorophosphate;
palladium on activated charcoal;
In
tetrahydrofuran; nitromethane; dichloromethane; water; N,N-dimethyl-formamide; toluene;