[CH:1]([NH:3][CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH3:13])[CH:7]=1)=O.P(Cl)(Cl)(Cl)(Cl)Cl.CCCCCC>ClCCl>[CH3:13][O:12][C:8]1[CH:7]=[C:6]2[C:11](=[CH:10][CH:9]=1)[CH:1]=[N:3][CH2:4][CH2:5]2A solution of 29.4 Kg of N-formyl-3-methoxyphenethylamine in 30 litres of dichloromethane was added over 90 minutes to a well-stirred slurry of 38.4 Kg of phosphorus pentachloride in 30 litres of dichloromethane. An exothermic reaction ensued, causing the solvent to reflux at 35°-38° C. After addition was complete, the reaction mixture was hydrolysed by the addition of a mixture of 90 Kg of ice and 30 litres of hexane. After cooling the aqueous layer was separated, made basic with 144 Kg of 45% potassium hydroxide and extracted twice with 50 Kg of dichloromethane. After drying the organic layer with sodium sulfate the solvent was removed under reduced pressure to give 23 Kg of 6-methoxy-3,4-dihydroisoquinoline as an oil.
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