Dimethylformamide → HCID 10045043, compound

HRID 1588732Notes

Reaction equation

HRID 1588732 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][C:19]=1[Cl:24].[C:25](=O)([O-])[O-].[K+].[K+].CN(C)C=O.CI>O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:25])[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][C:19]=1[Cl:24]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 11726135HCID 11726135, compound

Product 1

HCID 10045043HCID 10045043, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of ethyl 6-chloro-4-(2-chlorophenyl)-1,2-dihydro-2-oxo-3-quinolinecarboxylate(1.81 g), potassium carbonate powder (0.7 g), and N,N-dimethylformamide (DMF) (20 ml) was dropwise added methyl iodide (0.37 g) under stirring. The mixture was stirred for 2.5 hours, diluted with water and then extracted with ethyl acetate. The extract was washed with water, dried (MgSO4) and distilled to remove the solvent. The residue was crystallized with isopropyl ether to obtain ethyl 6-chloro-4-(2-chlorophenyl)-1,2-dihydro-1-methyl-2-oxo-3-quinolinecarboxylate. Recrystallization from ethanol gave colorless prisms. mp 139°-140° C.

Workup

  1. stirringThe mixture was stirred for 2.5 hours
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried (MgSO4)
  5. distillationdistilled
  6. customto remove the solvent
  7. customThe residue was crystallized with isopropyl ether

Sources & evidence

ORD record
ord-e9e6ef069ff7452e9f59f043ba07dca9
Source dataset
uspto-grants-1993_06
Patent number
US05223513

Reaction notes

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