2,3-dicyano-5,6-dichloro-p-benzoquinone in toluene 2 h; Heating;

1: 56 percent / dichlorodicyanobenzoquinone (DDQ) / toluene / 2 h / Heating 2: 95 percent / hydrazine monohydrate / Raney Ni / ethanol / 2 h / Heating View Scheme

<b>Multi-step reaction with 7 steps<br /> </b>2: 95 percent / 20percent aq. KOH / ethanol / 48 h / Heating<br />3: thionyl chloride (SOCl₂) / 1 h / Heating<br />4: AlCl₃ / CH₂Cl₂ / 0.33 h / 0 &deg;C<br />5: 16 percent / ammonium nitrate, trifluoroacetic anhydride / acetonitrile / Ambient temperature<br />6: NaBH₄ / CH₂Cl₂; methanol / 2 h / Ambient temperature<br />7: p-toluenesulfonic acid / toluene / 3 h / Heating<br /> <br /> &nbsp;