Ethylene carbonate → 2-(2-Amino-8-quinolinyloxy)-ethanol

HRID 991669Notes

Reaction equation

HRID 991669 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([OH:12])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.C1(=O)O[CH2:16][CH2:15][O:14]1.O(C(C)(C)C)[K]>CN(C=O)C.[Cl-].[Na+].O>[NH2:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([O:12][CH2:16][CH2:15][OH:14])[CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

6

Reactant 3

HCID 7303Ethylene carbonateHCID 46537882-Amino-8-quinolinolHCID 178418922HCID 178418922, compound

Product 1

HCID 220362542-(2-Amino-8-quinolinyloxy)-ethanolYield 28%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2-amino-8-quinolinol (3.20 g, 20.0 mmol), ethylene carbonate (1.76 g, 20.0 mmol) and KO-t-Bu (2.24 g, 20.0 mmol) in DMF (20 mL) was stirred at 90° C. for 15 h. The mixture was poured into brine, extracted with EtOAc, dried (MgSO4), and concentrated under reduced pressure. The residue was purified by chromatography on silica gel using toluene/EtOAc/MeOH (50:50:2) as eluent to give 1.13 g (28%) of the title product as a solid. HRMS m/z calcd for C11H12N2O2 (M)+ 204.0899, found 204.0906.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-8dab482e02cc4698871717c6ac81236d
Source dataset
uspto-grants-2002_10
Patent number
US06465467B1

Reaction notes

Loading…