Dimethyl Sulfoxide → Ethyl 2-[1-(4-chlorophenyl)isoquinolin-5-yl]-2-cyanopropionate

HRID 1156883Notes

Reaction equation

HRID 1156883 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[CH:16]=[CH:15][CH:14]=[C:13]([CH2:18][C:19]#[N:20])[C:12]=3[CH:11]=[CH:10][N:9]=2)=[CH:4][CH:3]=1.[H-].[Na+].CS(C)=O.[CH3:27]I.[C:29](=O)([O:33]CC)[O:30][CH2:31][CH3:32]>O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[C:13]([C:18]([C:19]#[N:20])([CH3:27])[C:29]([O:30][CH2:31][CH3:32])=[O:33])[CH:14]=[CH:15][CH:16]=3)[CH:11]=[CH:10][N:9]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 679Dimethyl SulfoxideHCID 6328Methyl iodideHCID 7766Diethyl CarbonateHCID 24758Sodium hydrideHCID 128518281-(4-Chlorophenyl)isoquinoline-5-acetonitrile

Product 1

HCID 20533893Ethyl 2-[1-(4-chlorophenyl)isoquinolin-5-yl]-2-cyanopropionate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

1-(4-Chlorophenyl)isoquinoline-5-acetonitrile (2.6 g) was dissolved in 20 ml of diethyl carbonate, and 1.0 g of 50% oily sodium hydride was added. Then, 10 ml of dimethylsulfoxide was added, and 1.5 g of methyl iodide was added under cooling with water. The mixture was stirred for 1 hour. The reaction mixture was poured into water, extracted with ether, and dried. The solvent was distilled off. The resulting oily product was recrystallized from ether-hexane to afford ethyl 2-[1-(4-chlorophenyl)isoquinolin-5-yl]-2-cyanopropionate as colorless prisms having a melting point of 92° to 93.5° C.

Workup

  1. extractionextracted with ether
  2. customdried
  3. distillationThe solvent was distilled off
  4. customThe resulting oily product was recrystallized from ether-hexane

Sources & evidence

ORD record
ord-00bd71bee49344ee8774d1cfeb8d95ca
Source dataset
uspto-grants-1982_06
Patent number
US04337256

Reaction notes

Loading…