Water → 1-(4-Methylphenyl)isoquinoline-5-acetonitrile

Reaction equation

[C-:1]#[N:2].[Na+].[CH3:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:20]3[C:15](=[C:16]([CH2:21]Cl)[CH:17]=[CH:18][CH:19]=3)[CH:14]=[CH:13][N:12]=2)=[CH:7][CH:6]=1.O>CS(C)=O>[CH3:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:20]3[CH:19]=[CH:18][CH:17]=[C:16]([CH2:21][C:1]#[N:2])[C:15]=3[CH:14]=[CH:13][N:12]=2)=[CH:7][CH:6]=1

Participants

Procedure

Sodium cyanide (1.89 g) was dissolved in 100 ml of dimethylsulfoxide, and 8.6 g of 1-(4-methylphenyl)-5-chloromethylisoquinoline was added. At room temperature, the mixture was stirred for 1 hour. After the reaction, the reaction mixture was poured into water, extracted with ether, washed in water, and dried. The solvent was distilled off. The residue was recrystallized from ether to afford 7 g of 1-(4-methylphenyl)isoquinoline-5-acetonitrile as prisms having a melting point of 101.7° to 102.1° C.