Methyl iodide → HCID 22493575, compound

HRID 1816311Notes

Reaction equation

HRID 1816311 reaction equation
[CH:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[N:12]=[C:11]([C:14]([O:16][CH3:17])=[O:15])[CH:10]=[CH:9]2)([CH3:3])[CH3:2].[C:18](=O)([O-])[O-:19].[K+].[K+].CI.C(OCC)(=O)C.CCCCCC>CN(C)C=O>[CH:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[N:12]=[C:11]([C:14]([O:16][CH3:17])=[O:15])[CH:10]=[C:9]2[O:19][CH3:18])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 21226206Ethyl acetate hexaneHCID 22493619HCID 22493619, compound

Product 1

HCID 22493575HCID 22493575, compoundYield 89.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

In 10 ml of N,N-dimethylformamide were dissolved 700 mg of methyl 8-isopropylquinoline-2-carboxylate. To the resulting solution were added 1.2 g of potassium carbonate and 195 μl of methyl iodide, followed by stirring at 50° C. for one hour. The reaction mixture was extracted with ethyl acetate. The organic layer was successively washed with water and saturated saline, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue so obtained was subjected to chromatography on a silica gel column (developing solvent: 5% ethyl acetate/n-hexane), whereby 710 mg of the title compound were obtained in the form of a pale yellow solid.

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate
  2. washThe organic layer was successively washed with water and saturated saline
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue so obtained

Sources & evidence

ORD record
ord-73de6bcbed6549939d0f636dd3407042
Source dataset
uspto-grants-2005_04
Patent number
US06884808B2

Reaction notes

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