Methyl iodide → Ethyl 6-chloro-1,2-dihydro-1-methyl-2-oxo-4-phenyl-3-quinolinecarboxylate

HRID 1588736Notes

Reaction equation

HRID 1588736 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[C:6]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:5]2[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[H-].[Na+].[CH3:26]I>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:26])[C:7](=[O:12])[C:6]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:5]2[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 738703Ethyl 6-chloro-2-oxo-4-phenyl-1,2-dihydro-3-quinolinecarboxylate

Product 1

HCID 10405076Ethyl 6-chloro-1,2-dihydro-1-methyl-2-oxo-4-phenyl-3-quinolinecarboxylateYield 162.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of ethyl 6-chloro-1,2-dihydro-2-oxo-4-phenyl-3-quinolinecarboxylate (2.62 g) and DMF (24 ml) was added portionwise 60% sodium hydride in oil (0.35 g), followed by stirring for 30 minutes at room temperature. The mixture was ice-cooled, to which methyl iodide (0.6 g) was dropwise added under stirring. The mixture was stirred for 3 hours at room temperature, diluted with and extracted with ethyl acetate. The extract was washed with water, dried (MgSO4) and concentrated to remove the solvent. The residue was crystallized from isopropyl ether to give crystals of ethyl 6-chloro-1,2-dihydro -1-methyl-2-oxo-4-phenyl-3-quinolinecarboxylate (2.35 g, 92.7%). Recrystallization from ethanol gave colorless needles. mp 124°-125° C.

Workup

  1. additionwas dropwise added
  2. stirringunder stirring
  3. stirringThe mixture was stirred for 3 hours at room temperature
  4. additiondiluted with and
  5. extractionextracted with ethyl acetate
  6. washThe extract was washed with water
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated
  9. customto remove the solvent
  10. customThe residue was crystallized from isopropyl ether

Sources & evidence

ORD record
ord-5cf1e672c1a34af69a19cea671d391dd
Source dataset
uspto-grants-1993_06
Patent number
US05223513

Reaction notes

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