Methyl iodide → Methyl 8-methoxyquinoline-2-carboxylate

HRID 2393092Notes

Reaction equation

HRID 2393092 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]([O:14][CH3:15])=[O:13])[CH:8]=[CH:7]2.[C:16](=O)([O-])[O-].[K+].[K+].IC>CC(C)=O>[CH3:16][O:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]([O:14][CH3:15])=[O:13])[CH:8]=[CH:7]2

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 12336161Methyl 8-Hydroxyquinoline-2-Carboxylate

Product 1

HCID 12336162Methyl 8-methoxyquinoline-2-carboxylateYield 100.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Methyl 8-hydroxyquinoline-2-carboxylate (1.6 g), acetone (15 ml), potassium carbonate (1.3 g) and iodomethane (0.6 ml) were combined and stirred at room temperature for 48 h. The solvents were removed in vacuo and the resulting white residue suspended in water (25 ml) which was extracted with ethyl acetate (3×25 ml). The combined organic layers were dried (magnesium sulphate) and the solvents removed in vacuo to give the title compound as a white solid (1.72 g).

Workup

  1. customThe solvents were removed in vacuo
  2. extractionwas extracted with ethyl acetate (3×25 ml)
  3. dry with materialThe combined organic layers were dried (magnesium sulphate)
  4. customthe solvents removed in vacuo

Sources & evidence

ORD record
ord-374e71d9df9844cc84c39716c23cd704
Source dataset
uspto-grants-1998_09
Patent number
US05804588

Reaction notes

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