Water → Ethyl 1-cyclopropyl-6,7-difluoro-8-methyl-5-nitro-4-oxo-1,4-dihydroquinoline-3-carboxylate

HRID 342618Notes

Reaction equation

HRID 342618 reaction equation
[CH:1]1([NH:4][CH:5]=[C:6]([C:12](=[O:26])[C:13]2[C:18]([N+:19]([O-:21])=[O:20])=[C:17]([F:22])[C:16]([F:23])=[C:15]([CH3:24])[C:14]=2F)[C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:3][CH2:2]1.[H-].[Na+].O>O1CCOCC1>[CH:1]1([N:4]2[C:14]3[C:13](=[C:18]([N+:19]([O-:21])=[O:20])[C:17]([F:22])=[C:16]([F:23])[C:15]=3[CH3:24])[C:12](=[O:26])[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5]2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 962WaterHCID 24758Sodium hydrideHCID 178471886HCID 178471886, compound

Product 1

HCID 10736705Ethyl 1-cyclopropyl-6,7-difluoro-8-methyl-5-nitro-4-oxo-1,4-dihydroquinoline-3-carboxylateYield 76%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 27.1 g of ethyl 3-cyclopropylamino-2-(2,4,5-trifluoro-3-methyl-6-nitrobenzoyl)acrylate in 270 ml of dioxane, 3.2 g of 60% sodium hydride was added, and then stirring was continued for 1 hour at room temperature. Water (300 ml) was added to the reaction mixture, and then the crystals precipitated were collected by filtration to obtain 19.5 g of colorless crystals. The crystals were. recrystallized from N,N-dimethylformamide to colorless needles, m.p. 260°-263° C.

Workup

  1. customthe crystals precipitated
  2. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-62439138a7db4c66a17796ac30412390
Source dataset
uspto-grants-1999_01
Patent number
US05859026

Reaction notes

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