1: 90 percent / K2CO3 / dimethylformamide / 3 h / 40 °C 2: 86.3 percent / H2 / 10 percent Pd/C / ethanol; dioxane / 0.75 h / 20 °C / 2280 Torr 3: 77.2 percent / iPr2EtN / CH2Cl2 / Ambient temperature 4: 87.5 percent / 1 N aq. NaOH / dioxane; methanol / 14 h / 20 °C View Scheme

Stage #1: <a href="#" onclick="return RXDsubstances(event, this, '777186', constants.ctx, '0')">meta-nitrobenzoyl chloride</a> <b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1209238', constants.ctx, '0')">aluminium trichloride</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1730800', constants.ctx, '0')">dichloromethane</a> <br />T=20&deg;C;&nbsp;0.166667&nbsp;h;&nbsp;<br />Stage #2: <a href="#" onclick="return RXDsubstances(event, this, '107693', constants.ctx, '0')">indole</a> &nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1730800', constants.ctx, '0')">dichloromethane</a> <br />Friedel-Crafts acylation;&nbsp;1&nbsp;h;&nbsp;<br /> &nbsp;