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

HRID 1078267Notes

Reaction equation

HRID 1078267 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 1,4-dioxane, 3.2 g of sodium hydride (60% mineral oil dispersion) was added by portions and stirred at room temperature for one hour. 300 ml of water was added to the reaction mixture and the deposited crystals were collected by filtration to give 19.5 g of the desired compound as colorless crystals, which was recrystallized from N,N-dimethylformamide to provide colorless needles, m.p. 260°-263° C.

Workup

  1. filtrationthe deposited crystals were collected by filtration

Sources & evidence

ORD record
ord-9f19ec4c810340dabf3e51866a232595
Source dataset
uspto-grants-1996_08
Patent number
US05547962

Reaction notes

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