1: 45 percent / KOH / dimethylsulfoxide / 5 h / Ambient temperature 2: 70 percent / NaH / dimethylformamide; CH2Cl2 / 5 h / Ambient temperature 3: 72 percent / H2 / 10percent Pd/C / methanol / 2 h / 760 Torr / Ambient temperature View Scheme

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '107477', constants.ctx, '0')">quinoline</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '3587189', constants.ctx, '0')">hydrogen</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '11378922', constants.ctx, '0')">palladium on activated charcoal</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1718733', constants.ctx, '0')">ethanol</a> <br />P=760&nbsp;Torr;&nbsp;1&nbsp;h;&nbsp;&nbsp;Ambient temperature;&nbsp;<br /> &nbsp;

<b>Multi-step reaction with 5 steps<br /> </b>1: NaBH₄ / methanol / 0.5 h / 0 &deg;C<br />2: 1 N NaOH / tetrahydrofuran / 1 h / Ambient temperature<br />3: 64 percent / 1-&lt;3-(dimethylamino)propyl&gt;-3-ethylcarbodiiimide / tetrahydrofuran; H₂O / 1 h / Ambient temperature<br />4: Ph₃P, diethylazodicarboxylate / tetrahydrofuran / 16 h / Ambient temperature<br />5: 93 percent / quinoline, H₂ / 5percent Pd/C / ethanol / 1 h / 760 Torr / Ambient temperature<br /> <br /> &nbsp;