Multi-step reaction with 28 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: 95 percent / cc. H2SO4 / toluene
11: 99 percent / B2H6 / tetrahydrofuran
12: 86 percent / 48 percent HBr / H2O / 0.5 h / Heating
13: 1.) Na / 1.) ethanol; 2.) ethanol, reflux
14: H2O, KOH / Heating
15: diethylformamide / Heating
16: SOCl2 / Heating
17: SnCl2 / CH2Cl2; nitromethane / Ambient temperature
18: B2H6 / tetrahydrofuran
19: PhCH2ONa / Heating
20: H2, triethylamine / 10 percent Pd/C / tetrahydrofuran / Ambient temperature
21: dimethylformamide / Heating
22: POCl3 / CH2Cl2
23: NaHCO3 / H2O / Heating
24: cyclohexylamine / toluene / Heating
25: SO2Cl2 / CH2Cl2 / Ambient temperature
26: glacial acetic acid / 80 °C
27: H2O, KOH / propan-1-ol / Heating
28: dimethylformamide / Heating
With
quinoline; potassium hydroxide; thionyl chloride; sulfuryl dichloride; N-ethylpropionamide; 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; propan-1-ol; nitromethane; dichloromethane; water; N,N-dimethyl-formamide; toluene;