hydrogenchloride in methanol T=4°C; 3 h;

acetic acid T=60°C; 6 h;

1: 54 percent / pyridinium p-toluenesulfonate / methanol / 6 h / 55 °C 2: 82 percent / pyridine / CH2Cl2 / 5 h / Ambient temperature View Scheme

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '11604118', constants.ctx, '0')">tetrakis(triphenylphosphine) palladium⁽⁰⁾</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '102391', constants.ctx, '0')">tetrahydrofuran</a> <br />&nbsp;Ambient temperature;&nbsp;<br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1: 85 percent / lithium amide / liquid ammonia; tetrahydrofuran<br />2: H₂; quinoline / 5 percent Pd/BaSO₄ / hexane / 24 h / 40 &deg;C / 1034.3 Torr<br /> <br /> &nbsp;

<b>Multi-step reaction with 4 steps<br /> </b>1: 70 percent / hydrobromic acid / benzene; H₂O / 72 h / Heating<br />2: 89 percent / conc. hydrochloric acid / diethyl ether / 14 h / 0 - 20 &deg;C<br />3: 85 percent / lithium amide / liquid ammonia; tetrahydrofuran<br />4: H₂; quinoline / 5 percent Pd/BaSO₄ / hexane / 24 h / 40 &deg;C / 1034.3 Torr<br /> <br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1: 89 percent / conc. hydrochloric acid / diethyl ether / 14 h / 0 - 20 &deg;C<br />2: 85 percent / lithium amide / liquid ammonia; tetrahydrofuran<br />3: H₂; quinoline / 5 percent Pd/BaSO₄ / hexane / 24 h / 40 &deg;C / 1034.3 Torr<br /> <br /> &nbsp;