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

HRID 991648Notes

Reaction equation

HRID 991648 reaction equation
[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>[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

Participants

5

Reactant 3

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

Product 1

HCID 220362412-(Isoquinolin-5-yloxy)ethanolYield 67.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
155 °C

Procedure

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 CHCl13 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.

Workup

  1. temperatureAfter cooling
  2. additionthe mixture was diluted with CHCl13
  3. filtrationfiltered through a pad of Celite
  4. concentrationThe brownish filtrate was concentrated in vacuo
  5. customthe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-fe83062281e1464ea249e6ccf8dc4817
Source dataset
uspto-grants-2002_10
Patent number
US06465467B1

Reaction notes

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