8-Hydroxyquinoline → Ethyl (quinolin-8-yloxy)acetate

HRID 1507045Notes

Reaction equation

HRID 1507045 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[OH:11])[CH:4]=[CH:3][CH:2]=1.Br[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15].C([O-])([O-])=O.[K+].[K+]>CC#N>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[O:11][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 19238-HydroxyquinolineHCID 7748Ethyl bromoacetateHCID 11430Potassium Carbonate

Product 1

HCID 4379860Ethyl (quinolin-8-yloxy)acetateYield 81%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of quinolin-8-ol (3 g, 0.0207 mol) in MeCN (10 mL) was added ethyl bromoacetate (4.12 g, 0.025 mol) and K2CO3 (5.75 g, 0.0414 mol). The mixture was stirred at 80° C. for 12 h, filtered and concentrated. The residue was purified by column chromatography. (3.9 g, yield 81%) MS (ESI+) e/z: 232.1 [M+1]+.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-d6ebff954b54486c918a6e66f85357f0
Source dataset
uspto-grants-2015_12
Patent number
US09221794B2

Reaction notes

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