Methyl iodide → 8-Bromo-7-methoxyquinoline

HRID 2063554Notes

Reaction equation

HRID 2063554 reaction equation
[Br:1][C:2]1[C:3]([OH:12])=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.[C:13](=O)([O-])[O-].[K+].[K+].CI>CC(C)=O>[Br:1][C:2]1[C:3]([O:12][CH3:13])=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 1358901048-Bromo-7-hydroxyquinoline

Product 1

HCID 510630338-Bromo-7-methoxyquinolineYield 57.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 8-bromo-7-hydroxyquinoline (65 g, 0.29 mol), potassium carbonate (120 g, 0.87 mol), and methyl iodide (82 g, 0.58 mol) in acetone (500 mL) was heated to reflux for 4 hrs. The mixture was then cooled to rt and filtered. The filtrate was concentrated, dissolved in ethyl acetate (1 L), washed with water (300 mL×2) and saline (200 mL), dried over Na2SO4 and concentrated. The residue was recrystallized in ethyl acetate and hexane (1:1) to give 8-bromo-7-methoxyquinoline (40 g).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 4 hrs
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. dissolutiondissolved in ethyl acetate (1 L)
  6. washwashed with water (300 mL×2) and saline (200 mL)
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated
  9. customThe residue was recrystallized in ethyl acetate

Sources & evidence

ORD record
ord-370bb35388994557b2fecbcdbacbeefc
Source dataset
uspto-grants-2012_10
Patent number
US08288373B2

Reaction notes

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