Sodium hydride → Ethyl 6,7,8-trifluoro-1-(2,4-difluorophenyl)-1,4-dihydro-5-methyl-4-oxo-3-quinolinecarboxylate

HRID 2073832Notes

Reaction equation

HRID 2073832 reaction equation
[F:1][C:2]1[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:3]=1[NH:4][CH:5]=[C:6]([C:12](=[O:24])[C:13]1[C:18]([CH3:19])=[C:17]([F:20])[C:16]([F:21])=[C:15]([F:22])[C:14]=1F)[C:7]([O:9][CH2:10][CH3:11])=[O:8].[H-].[Na+]>C1COCC1>[F:20][C:17]1[C:18]([CH3:19])=[C:13]2[C:14](=[C:15]([F:22])[C:16]=1[F:21])[N:4]([C:3]1[CH:25]=[CH:26][C:27]([F:29])=[CH:28][C:2]=1[F:1])[CH:5]=[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:12]2=[O:24]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 178471929HCID 178471929, compound

Product 1

HCID 14651271Ethyl 6,7,8-trifluoro-1-(2,4-difluorophenyl)-1,4-dihydro-5-methyl-4-oxo-3-quinolinecarboxylateYield 58.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cold (5° C.) solution of 2.77 g (6.64 mmol) of ethyl 3-(2,4-difluoroanilino)-2-(2,3,4,5-tetrafluoro-6-methylbenzoyl)acrylate in 60 ml of dry THF was added 0.32 g of 60% sodium hydride. The solution was stirred overnight at room temperature, then concentrated to an orange foam. The residue was partitioned between methylene chloride and 1N HCl. The organic phase was washed with water, dried over magnesium sulfate, and concentrated to an orange solid which was recrystallized (ethyl acetate:hexane) to give 1.55 g of the title compound, mp 152°-154° C.

Workup

  1. concentrationconcentrated to an orange foam
  2. customThe residue was partitioned between methylene chloride and 1N HCl
  3. washThe organic phase was washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated to an orange solid which
  6. customwas recrystallized (ethyl acetate:hexane)

Sources & evidence

ORD record
ord-14d46361b3284f35a2b109ccccd2f23d
Source dataset
uspto-grants-1990_04
Patent number
US04920120

Reaction notes

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