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

HRID 1278Notes

Reaction equation

HRID 1278 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 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 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-8baad9aabd414b21a6bb786ba650a995
Source dataset
uspto-grants-1998_03
Patent number
US05723648

Reaction notes

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