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

HRID 2271274Notes

Reaction equation

HRID 2271274 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

2.6 g of ethyl 2-(2-methyl-3,4,6-trifluorobenzoyl)-3-cyclopropylaminoacrylate was dissolved in 26 ml of anhydrous dioxane, and thereto 0.38 g of 60% sodium hydride was added portionwise under ice-cooling. After stirring at room temperature for 30 minutes, the mixture was poured into ice water and extracted with dichloromethane. The extract was dried over magnesium sulfate and concentrated. Diethyl ether was added to the residue and the resulting crystals were filtered, followed by recrystallization from ethanol to give 2.0 g of ethyl 1-cyclopropyl-6,7-difluoro-5-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylate.

Workup

  1. temperaturecooling
  2. extractionextracted with dichloromethane
  3. dry with materialThe extract was dried over magnesium sulfate
  4. concentrationconcentrated
  5. additionDiethyl ether was added to the residue
  6. filtrationthe resulting crystals were filtered
  7. customfollowed by recrystallization from ethanol

Sources & evidence

ORD record
ord-a79846aeb61641548ac599ac27dfaf8a
Source dataset
uspto-grants-2001_12
Patent number
US06333431B1

Reaction notes

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