1: thionyl chloride / 1 h / 50 °C 2: 1.) triethylamine; 2.) 20percent HCl / 1.) chloroform, 35 deg C, 5 h; 2.) chloroform, reflux, 5 h 3: sodium hydroxide / ethanol / 1 h / Heating 4: 1.) hydrazine hydrate; 2.) potassium hydroxide / 1.) triethanolamine, 130 deg C; reflux, 4 h; 2.) triethanolamine, 200 deg C, 9 h View Scheme

1: 1.) triethylamine; 2.) 20percent HCl / 1.) chloroform, 35 deg C, 5 h; 2.) chloroform, reflux, 5 h 2: sodium hydroxide / ethanol / 1 h / Heating 3: 1.) hydrazine hydrate; 2.) potassium hydroxide / 1.) triethanolamine, 130 deg C; reflux, 4 h; 2.) triethanolamine, 200 deg C, 9 h View Scheme

1: Br2 / CCl4 2: Na, liq. NH3, Fe(NO3)3 / diethyl ether 3: (i) Na, liq. NH3, (ii) /BRN= 1071199/ 4: (i) aq. EtOH, (ii) NaOH 5: H2 / Raney-Ni View Scheme

1: Na, liq. NH3, Fe(NO3)3 / diethyl ether 2: (i) Na, liq. NH3, (ii) /BRN= 1071199/ 3: (i) aq. EtOH, (ii) NaOH 4: H2 / Raney-Ni View Scheme

hydrogen; platinum

1: (i) Na, liq. NH3, (ii) /BRN= 1071199/ 2: (i) aq. EtOH, (ii) NaOH 3: H2 / Raney-Ni View Scheme

1: (i) aq. EtOH, (ii) NaOH 2: H2 / Raney-Ni View Scheme