Sodium hydride → Ethyl 1-cyclopropyl-6,7,8-trifluoro-5-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylate

HRID 232659Notes

Reaction equation

HRID 232659 reaction equation
[CH3:1][C:2]1[C:7]([C:8]([C:10](=[CH:16][NH:17][CH:18]2[CH2:20][CH2:19]2)[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[O:9])=[C:6](F)[C:5]([F:22])=[C:4]([F:23])[C:3]=1[F:24].[H-].[Na+]>O1CCOCC1>[CH:18]1([N:17]2[C:6]3[C:7](=[C:2]([CH3:1])[C:3]([F:24])=[C:4]([F:23])[C:5]=3[F:22])[C:8](=[O:9])[C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:16]2)[CH2:20][CH2:19]1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 178471859ethyl 3-(cyclopropylamino)-2-(2,3,4,5-tetrafluoro-6-methylbenzoyl)prop-2-enoate

Product 1

HCID 14651259Ethyl 1-cyclopropyl-6,7,8-trifluoro-5-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylateYield 98.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Ethyl 2-(6-methyl-2,3,4,5-tetrafluorobenzoyl)-3-cyclopropylaminoacrylate (4.50 g) is dissolved in anhydrous dioxane (26 ml) and thereto 60% sodium hydride (580 mg) is gradully added under ice-cooling. After stirring at room temperature for 30 minutes, the reaction mixture is poured into ice-water and extracted with dichloromethane. The extract is dried over magnesium sulfate and concentrated. The residue is added with diethyl ether and crystals are filtered, which are recrystalized from dichloromethane-n-hexane to give ethyl 1-cyclopropyl-6,7,8-trifluoro-5-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylate (4.19 g), as white needles, m.p. 180°-183° C.

Workup

  1. temperaturecooling
  2. extractionextracted with dichloromethane
  3. dry with materialThe extract is dried over magnesium sulfate
  4. concentrationconcentrated
  5. additionThe residue is added with diethyl ether and crystals
  6. filtrationare filtered
  7. customwhich are recrystalized from dichloromethane-n-hexane

Sources & evidence

ORD record
ord-6865d71fb9744f5f898ccd2e1ee93d91
Source dataset
uspto-grants-1997_01
Patent number
US05591744

Reaction notes

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