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

HRID 1156885
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1156885
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
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962
Water
Lösungsmittel
2×

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-dc634eaedd4344ddb380f8d353482e78
Quelldatensatz
uspto-grants-1982_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04337256

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