Ethylene carbonate → 2-(Isoquinolin-5-yloxy)ethanol

HRID 493304

Reaktionsgleichung

Reaktionsgleichung von HRID 493304
[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]=[CH:7]2.C1(=O)O[CH2:15][CH2:14][O:13]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.C(Cl)(Cl)Cl>[CH:7]1[C:8]2[C:3](=[C:2]([O:1][CH2:15][CH2:14][OH:13])[CH:11]=[CH:10][CH:9]=2)[CH:4]=[CH:5][N:6]=1

Komponenten

6

Edukt 3

HCID 7303Ethylene carbonateHCID 11430Potassium CarbonateHCID 30386Isoquinolin-5-ol

Produkt 1

HCID 220362412-(Isoquinolin-5-yloxy)ethanolAusbeute 67,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212ChloroformLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
155 °C

Versuchsvorschrift

A mixture of 5-hydroxyisoquinoline (2.05 g, 14.1 mmol), ethylene carbonate (1.43 g, 16.2 mmol), K2CO3 (0.97 g, 7.1 mmol) in DMF (6 mL) was heated at 155° C. for 1.5 h under stirring in a sealed tube. After cooling, the mixture was diluted with CHCl3 and filtered through a pad of Celite. The brownish filtrate was concentrated in vacuo, and the residue was purified by chromatography on silica gel using EtOAc as eluent to give 1.8 g (67%) of the title product as a beige oil which solidified on standing: mp 64-67° C., HRMS m/z calcd for C11H11NO2 (M)+ 189.0790, found 189.0789. Anal. (C11H11NO2) C, H, N.

Aufarbeitung

  1. temperatureAfter cooling
  2. filtrationfiltered through a pad of Celite
  3. concentrationThe brownish filtrate was concentrated in vacuo
  4. customthe residue was purified by chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-e1e77ea3058a47a7bf3279e96775c75b
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07534794B2

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