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

HRID 864334Notes

Reaction equation

HRID 864334 reaction equation
[CH3:1][C:2]1[C:20]([F:21])=[C:19]([F:22])[CH:18]=[C:17](F)[C:3]=1[C:4]([C:6](=[CH:12][NH:13][CH:14]1[CH2:16][CH2:15]1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:5].[H-].[Na+]>O1CCOCC1>[CH:14]1([N:13]2[C:17]3[C:3](=[C:2]([CH3:1])[C:20]([F:21])=[C:19]([F:22])[CH:18]=3)[C:4](=[O:5])[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:12]2)[CH2:16][CH2:15]1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 178418304HCID 178418304, compound

Product 1

HCID 14651255Ethyl 1-cyclopropyl-6,7-difluoro-5-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylateYield 81.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Ethyl 2-(2-methyl-3,4,6-trifluorobenzoyl)-3-cyclopropylaminoacrylate (2.6 g) is dissolved in anhydrous dioxane (26 ml) and thereto 60% sodium hydride (0.38 g) is gradually 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 ethanol to give ethyl 1-cyclopropyl-6,7-difluoro-5-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylate (2.0 g), m.p. 185°-187° 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 ethanol

Sources & evidence

ORD record
ord-9390ae9e6fdf4e6ab856e9ce8de000e8
Source dataset
uspto-grants-1996_10
Patent number
US05563138

Reaction notes

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