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

HRID 1156903Notes

Reaction equation

HRID 1156903 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

5

Reactant 3

HCID 962WaterHCID 8929Sodium CyanideHCID 12851845HCID 12851845, compound

Product 1

HCID 128518461-(4-Methylphenyl)isoquinoline-5-acetonitrileYield 84.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

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.

Workup

  1. customAfter the reaction
  2. extractionextracted with ether
  3. washwashed in water
  4. customdried
  5. distillationThe solvent was distilled off
  6. customThe residue was recrystallized from ether

Sources & evidence

ORD record
ord-58ea6b15981d459aac30441c3d326c73
Source dataset
uspto-grants-1982_06
Patent number
US04337256

Reaction notes

Loading…