1: p-TsOH / toluene / 12 h / Heating 2: 1.) hydroquinone, 2.) 20percent AcOH / 1.) THF, 60 deg C, 2 d,2.) H2O, THF, 40 deg C, 72 h 3: 76 percent / LiOH, 30percent H2O2 / methanol / 5 h / 20 °C 4: 1.) NH2NH2*H2O, 2.) KOH, 3.) conc. HCl / 1.) diethylene glycol, 160 deg C, 1 h, 2.) 220-225 deg C, 4 h, 3.) H2O, 0 deg C, 4.) Et2O, 0 deg C 5: 1.) POCl3, 2.) 1M LiClO4, 3.) H2, 4.) 30percent ammonia / 3.) 10percent Pd/C / 1.) CH3CN, 100 deg C, 4 h, 2.) CH2Cl2, 10 min, 3.) DMF, 1 bar, 5 h 6: 70 percent / sodium bis(trimethylsilyl)amide / toluene; tetrahydrofuran / 2 h / 20 °C 7: 65 percent / tert-butyl nitrite, sodium bis(trimethylsilyl)amide / toluene; tetrahydrofuran / 1.5 h / 50 °C 8: p-TsOH, paraformaldehyde / acetic acid / 5 h / 100 - 105 °C 9: 40 percent / t-BuOK / 2 h / 20 °C View Scheme

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '3587155', constants.ctx, '0')">water</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '8128145', constants.ctx, '0')">lithium bromide</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '605365', constants.ctx, '0')">N,N-dimethyl-formamide</a> <br />12&nbsp;h;&nbsp;&nbsp;Heating;&nbsp;<br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1: 79 percent / NaH / tetrahydrofuran / 4 h / 20 &deg;C<br />2: 79 percent / LiBr, H₂O / dimethylformamide / 12 h / Heating<br /> <br /> &nbsp;

<b>Multi-step reaction with 4 steps<br /> </b>1: 83 percent / tetrahydrofuran / 12 h / 20 &deg;C<br />2: 83 percent / 1,4-bis(methylamino)pyridine, DCC / CH₂Cl₂ / 18 h / 20 &deg;C<br />3: 79 percent / NaH / tetrahydrofuran / 4 h / 20 &deg;C<br />4: 79 percent / LiBr, H₂O / dimethylformamide / 12 h / Heating<br /> <br /> &nbsp;