1: quinoline 2: (i) (reduction), (ii) TsCl, (iii) DMSO, NaHCO3 View Scheme

1: quinoline 2: H2SO4 View Scheme

1: 1.) 30 min, 150 deg; 2.) in 15 min to 180 deg C 2: H2SO4 / 1 h / Heating 3: 1.) LiAlH4; 2.) HCl / 1.) diethyl ether, 8 h, reflux; 2.) 0 deg C, water 4: pyridine / 1 h / 0 °C 5: LiBr / acetone / 5 h / Heating 7: KOH / ethanol; H2O / 5 h / Heating 8: 74 percent / N2H4*H2O, KOH / bis-(2-hydroxy-ethyl) ether; methanol / 125 deg C, 6 h; 195 deg C, 3 h View Scheme

1: 1.) 30 min, 150 deg; 2.) in 15 min to 180 deg C 2: H2SO4 / 1 h / Heating View Scheme

1: 1.) 30 min, 150 deg; 2.) in 15 min to 180 deg C 2: H2SO4 / 1 h / Heating 3: 1.) LiAlH4; 2.) HCl / 1.) diethyl ether, 8 h, reflux; 2.) 0 deg C, water View Scheme

1: 1.) 30 min, 150 deg; 2.) in 15 min to 180 deg C 2: H2SO4 / 1 h / Heating 3: 1.) LiAlH4; 2.) HCl / 1.) diethyl ether, 8 h, reflux; 2.) 0 deg C, water 4: pyridine / 1 h / 0 °C 5: LiBr / acetone / 5 h / Heating View Scheme