Methyl iodide → HCID 15678870, compound

HRID 258077Notes

Reaction equation

HRID 258077 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=[O:13])[CH2:7][CH:6]2[CH2:14][C:15]([O:17][CH3:18])=[O:16].[H-].[Na+].[CH3:21]I>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH3:21])[C:8](=[O:13])[CH2:7][CH:6]2[CH2:14][C:15]([O:17][CH3:18])=[O:16]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 156788691,2,3,4-Tetrahydro-6-methoxy-2-oxo-4-quinoline acetic acid, methyl ester

Product 1

HCID 15678870HCID 15678870, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 40.8 g of 1,2,3,4-tetrahydro-6-methoxy-2-oxo-4-quinoline acetic acid, methyl ester in 500 ml of dimethyl formamide was added over 1 hour to a chilled (0° C.) suspension of 4.6 g of sodium hydride in 300 ml of dimethyl formamide. After stirring for 1 hour at ambient temperature, 27.5 g of methyl iodide was added and the mixture stirred for an additional hour. The mixture was then quenched with saturated ammonium chloride solution and extracted with ethyl acetate. The combined organic layers were washed with water and brine, dried over magnesium sulfate, filtered and concentrated to an oil. Column chromatography on silica gel (elution with hexane-ethyl acetate) afforded 1,2,3,4-tetrahydro-6-methoxy-1-methyl-2-oxo-4-quinoline acetic acid, methyl ester.

Workup

  1. temperaturea chilled
  2. stirringthe mixture stirred for an additional hour
  3. customThe mixture was then quenched with saturated ammonium chloride solution
  4. extractionextracted with ethyl acetate
  5. washThe combined organic layers were washed with water and brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated to an oil

Sources & evidence

ORD record
ord-8c46a1579ab646b7841ba7c4267b53fe
Source dataset
uspto-grants-1993_11
Patent number
US05264575

Reaction notes

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