Sodium hydride → Ethyl 1-[(1R,2S)-2-Fluorocyclopropyl]-6,7,8-trifluoro-5-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylate

HRID 1939267Notes

Reaction equation

HRID 1939267 reaction equation
[F:1][C@H:2]1[CH2:4][C@H:3]1[NH:5][CH:6]=[C:7]([C:13](=[O:25])[C:14]1[C:19]([CH3:20])=[C:18]([F:21])[C:17]([F:22])=[C:16]([F:23])[C:15]=1F)[C:8]([O:10][CH2:11][CH3:12])=[O:9].[H-].[Na+]>O1CCOCC1>[F:1][C@H:2]1[CH2:4][C@H:3]1[N:5]1[C:15]2[C:14](=[C:19]([CH3:20])[C:18]([F:21])=[C:17]([F:22])[C:16]=2[F:23])[C:13](=[O:25])[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6]1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 178472045HCID 178472045, compound

Product 1

HCID 70250897Ethyl 1-[(1R,2S)-2-Fluorocyclopropyl]-6,7,8-trifluoro-5-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylateYield 96.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

In 10 ml of anhydrous dioxane was dissolved 1.15 g of ethyl 3-[(1R,2S)-2-fluorocyclopropylamino]-2-(2,3,4,5-tetrafluoro-6-methylbenzoyl)acrylate, and 190 mg of 60% sodium hydride in oil was added thereto, followed by stirring at room temperature for 30 minutes. The dioxane was concentrated to about half the volume, and the concentrate was added to 25 ml of 1N hydrochloric acid under cooling with ice. The crystals precipitated were collected by filtration, washed with diethyl ether, and dried to yield 1.05 g of the titled compound as a yellow crystal.

Workup

  1. additionwas added
  2. concentrationThe dioxane was concentrated to about half the volume
  3. additionthe concentrate was added to 25 ml of 1N hydrochloric acid
  4. temperatureunder cooling with ice
  5. customThe crystals precipitated
  6. filtrationwere collected by filtration
  7. washwashed with diethyl ether
  8. customdried

Sources & evidence

ORD record
ord-8947a4fde6144b0d89174b01dfd75f79
Source dataset
uspto-grants-1997_12
Patent number
US05696132

Reaction notes

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