Potassium Carbonate → HCID 70983259, compound

HRID 338840Notes

Reaction equation

HRID 338840 reaction equation
[CH3:1][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.Br[CH2:14][CH:15]1[CH2:17][CH2:16]1.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH:15]1([CH2:14][O:12][C:5]2[CH:6]=[CH:7][CH:8]=[C:9]3[C:4]=2[N:3]=[C:2]([CH3:1])[CH:11]=[CH:10]3)[CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 132242-Methyl-8-hydroxyquinolineHCID 81503Bromomethylcyclopropane

Product 1

HCID 70983259HCID 70983259, compoundYield 98.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 2-methylquinolin-8-ol (10.0 g, 62.82 mmol), (bromomethyl)cyclopropane (17.0 g, 125.6 mmol), and K2CO3 (17.80 g, 128.8 mmol) in acetone (50 mL) in a sealed flask was stirred at 88° C. for 2 days. After cooling to ambient temperature, the acetone was removed under reduced pressure. DCM (100 mL) and water (50 mL) were added. The organic layer was separated, washed with brine, dried (sodium sulfate), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (DCM) to give 8-(cyclopropylmethoxy)-2-methylquinoline (13.2 g, 98.5%) as a solid.

Workup

  1. customthe acetone was removed under reduced pressure
  2. additionDCM (100 mL) and water (50 mL) were added
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried (sodium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by flash chromatography on silica gel (DCM)

Sources & evidence

ORD record
ord-8ab85f80b4d74890bf00e5601acb74d4
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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