1: NaNH2, liq. NH3 / tetrahydrofuran 2: NaNH2, liq. NH3 / tetrahydrofuran 3: (i) PhCO3H, (ii) HCO2H, (iii) KOH, H2O 4: H2, quinoline / Pd-BaSO4 / methanol 5: (i) Br2, (ii) HBr, AcOH, H2SO4 6: H2SO4 7: Zn, aq. HBr View Scheme