[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[C:13]([CH2:18]O)[CH:14]=[CH:15][CH:16]=3)[CH:11]=[CH:10][N:9]=2)=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)(Cl)[Cl:21].O.C(=O)([O-])[O-].[K+].[K+]>C(Cl)(Cl)Cl>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[C:13]([CH2:18][Cl:21])[CH:14]=[CH:15][CH:16]=3)[CH:11]=[CH:10][N:9]=2)=[CH:4][CH:3]=1
1-(4-Methylphenyl)-5-hydroxymethylisoquinoline (7.5 g) was dissolved in 80 ml of chloroform, and 12.5 g of phosphorus pentachloride was added under ice cooling. The mixture was stirred at room temperature for 1 hour, and 100 ml of water was added. The mixture was stirred for 30 minutes, and neutralized with potassium carbonate. The chloroform layer was washed in water, and dried. The solvent was distilled off, and the residue was recrystallized from methanol to afford 8.6 g of 1-(4-methylphenyl)-5-chloromethylisoquinoline as slightly yellow prisms having a melting point of 119.8° to 120.1° C.
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