Acetic Acid → 2-[1-(4-Chlorophenyl)isoquinolin-5-yl]propionic acid

HRID 1156885Notes

Reaction equation

HRID 1156885 reaction equation
C([O:3][C:4](=[O:26])[C:5]([C:9]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:10]=1[CH:11]=[CH:12][N:13]=[C:14]2[C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=1)(C#N)[CH3:6])C.S(=O)(=O)(O)O.C(O)(=O)C.[OH-].[Na+]>O>[Cl:25][C:22]1[CH:21]=[CH:20][C:19]([C:14]2[C:15]3[C:10](=[C:9]([CH:5]([CH3:6])[C:4]([OH:26])=[O:3])[CH:18]=[CH:17][CH:16]=3)[CH:11]=[CH:12][N:13]=2)=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 20533893Ethyl 2-[1-(4-chlorophenyl)isoquinolin-5-yl]-2-cyanopropionate

Product 1

HCID 128518642-[1-(4-Chlorophenyl)isoquinolin-5-yl]propionic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Ethyl-2-[1-(4-chlorophenyl)isoquinolin-5-yl]-2-cyanopropionate (1.0 g) was heated over an oil bath at 150° C. together with 2 ml of conc. sulfuric acid, 4 ml of acetic acid and 2 ml of water. After the reaction, the reaction mixture was poured into water. The pH of the mixture was adjusted to 4 with a 1 N aqueous solution of sodium hydroxide. The crystals that precipitated were extracted with dichloromethane, and dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was recrystallized from dichloromethane-hexane to afford 2-[1-(4-chlorophenyl)isoquinolin-5-yl]propionic acid as colorless prisms having a melting point of 199.5° to 202.0° C.

Workup

  1. customAfter the reaction
  2. customThe crystals that precipitated
  3. extractionwere extracted with dichloromethane
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off
  6. customthe residue was recrystallized from dichloromethane-hexane

Sources & evidence

ORD record
ord-dc634eaedd4344ddb380f8d353482e78
Source dataset
uspto-grants-1982_06
Patent number
US04337256

Reaction notes

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