Dimethylformamide → HCID 18959435, compound

HRID 1708549Notes

Reaction equation

HRID 1708549 reaction equation
CN(C)C=O.[C:6]([O:14][CH2:15][CH3:16])(=[O:13])[CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9].[H-].[Na+].Cl[CH2:20][N:21]([N:23]1[C:32]2[C:27](=[CH:28][C:29]([F:35])=[C:30]([F:34])[C:31]=2[F:33])[C:26](=[O:36])[C:25]([C:37]([O:39][CH2:40][CH3:41])=[O:38])=[CH:24]1)[CH3:22]>O.C(OCC)(=O)C>[F:35][C:29]1[CH:28]=[C:27]2[C:32](=[C:31]([F:33])[C:30]=1[F:34])[N:23]([N:21]([CH3:20])[CH2:22][CH:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:6]([O:14][CH2:15][CH3:16])=[O:13])[CH:24]=[C:25]([C:37]([O:39][CH2:40][CH3:41])=[O:38])[C:26]2=[O:36]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 7761Diethyl MalonateHCID 24758Sodium hydrideHCID 15247755HCID 15247755, compound

Product 1

HCID 18959435HCID 18959435, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To dimethylformamide (1.5 ml) solution of diethyl malonate (47.8 μl), was added sodium hydride (24.4 mg) with stirring under ice-cooling, and the mixture was stirred for 20 minutes with ice-cooling. To the solution was added ethyl 1-[N-(chloromethyl)-N-methylamino]-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate (100 mg) with stirring under ice-cooling, and the mixture was stirred for 30 minutes at the same temperature. The reaction solution was added to a mixed solution comprising ethyl acetate (30 ml) and water (30 ml) for extraction. The organic layer was washed with water (30 ml×3) and a saturated brine(30 ml×3), dried over magnesium sulfate and concentrated under reduced pressure. The residue thus obtained was subjected to column chromatography with silica gel (3 g), eluted with a mixed solvent of dichloromethane ethyl acetate (20/1 to 10/1) and concentrated to dryness under reduced pressure to obtain ethyl 6,7,8-trifluoro-1-[N-methyl-N-{2,2-bis(ethoxycarbonyl)ethyl}amino]-1,4-dihydro-4-oxoquinoline-3-carboxylate (49.1 mg).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred for 20 minutes with ice-
  3. temperaturecooling
  4. stirringwith stirring under ice-
  5. temperaturecooling
  6. stirringthe mixture was stirred for 30 minutes at the same temperature
  7. washThe organic layer was washed with water (30 ml×3)
  8. dry with materiala saturated brine(30 ml×3), dried over magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe residue thus obtained
  11. washeluted with a mixed solvent of dichloromethane ethyl acetate (20/1 to 10/1)
  12. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-1f066cdf411c4905a2762d2649c9384e
Source dataset
uspto-grants-1994_10
Patent number
US05359066

Reaction notes

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