Ethanol → 2-[1-(4-Chlorophenyl)isoquinolin-5-yl]propionitrile

HRID 1156884Notes

Reaction equation

HRID 1156884 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[C:13]([C:18]([C:25]#[N:26])(C)[C:19](OCC)=O)[CH:14]=[CH:15][CH:16]=3)[CH:11]=[CH:10][N:9]=2)=[CH:4][CH:3]=1.C(O)C.[OH-].[Na+]>O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[C:13]([CH:18]([CH3:19])[C:25]#[N:26])[CH:14]=[CH:15][CH:16]=3)[CH:11]=[CH:10][N:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 20533893Ethyl 2-[1-(4-chlorophenyl)isoquinolin-5-yl]-2-cyanopropionate

Product 1

HCID 128518392-[1-(4-Chlorophenyl)isoquinolin-5-yl]propionitrileYield 62.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ethyl 2-[1-(4-chlorophenyl)isoquinolin-5-yl]-2-cyanopropionate (1.0 g) was heated under reflux together with 40 ml of ethanol, 0.20 g of sodium hydroxide and 2 ml of water. After the reaction, the reaction mixture was concentrated under reduced pressure. The resulting oily product was extracted with ether, and dried. The solvent was distilled off, and the residue was recrystallized from ether-hexane to afford 0.5 g of 2-[1-(4-chlorophenyl)isoquinolin-5-yl]propionitrile as colorless needles having a melting point of 127.5° to 130° C.

Workup

  1. customAfter the reaction
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. extractionThe resulting oily product was extracted with ether
  4. customdried
  5. distillationThe solvent was distilled off
  6. customthe residue was recrystallized from ether-hexane

Sources & evidence

ORD record
ord-f30172f2cfa5468a97c14d44d6ff7add
Source dataset
uspto-grants-1982_06
Patent number
US04337256

Reaction notes

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