Water → HCID 86634195, compound

HRID 1669724Notes

Reaction equation

HRID 1669724 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[C:8]([OH:12])=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:20][CH2:21][O:22][CH3:23].O>CC(C)=O>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[O:12][CH2:20][CH2:21][O:22][CH3:23])[N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 809722-Bromoethyl methyl etherHCID 1354422212-chloroquinolin-5-ol

Product 1

HCID 86634195HCID 86634195, compoundYield 32.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
50 °C

Procedure

2-Chloro-quinolin-5-ol (CAS 124467-35-2) (0.3 g, 1.56 mmol) was dissolved in acetone (10 mL) and potassium carbonate (0.368 g, 2.75 mmol) was added. After addition of 2-bromethylmethylether (0.25 ml, 2.7 mmol) the reaction mixture was stirred for 18 h at 50° C. Then water was added and the mixture was extracted with ethyl acetate (3×). The combined organic phases were dried, filtered and concentrated. The residue was subjected to column chromatography (silica gel, heptane/ethyl acetate 9:1/4:1) to yield 2-chloro-5-(2-methoxy-ethoxy)-quinoline as a colourless oil (0.12 g, 30%). MS: m/e=238.8 (M+H+)

Workup

  1. extractionthe mixture was extracted with ethyl acetate (3×)
  2. customThe combined organic phases were dried
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-52db8e71b7d94c03953ac3b56d387714
Source dataset
uspto-grants-2011_08
Patent number
US07989628B2

Reaction notes

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