Water → Ethyl 1-cyclopropyl-6,7-difluoro-8-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylate

HRID 330084Notes

Reaction equation

HRID 330084 reaction equation
[H-].[Na+].F[C:4]1[C:22]([CH3:23])=[C:21]([F:24])[C:20]([F:25])=[CH:19][C:5]=1[C:6]([C:8](=[CH:14][NH:15][CH:16]1[CH2:18][CH2:17]1)[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:7].O>O1CCOCC1>[CH:16]1([N:15]2[C:4]3[C:5](=[CH:19][C:20]([F:25])=[C:21]([F:24])[C:22]=3[CH3:23])[C:6](=[O:7])[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:14]2)[CH2:18][CH2:17]1

Participants

5

Reactant 3

HCID 962WaterHCID 24758Sodium hydrideHCID 178471874HCID 178471874, compound

Product 1

HCID 9839540Ethyl 1-cyclopropyl-6,7-difluoro-8-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylateYield 78.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To the cooled mixture of 55% sodium hydride (50 mg) in anhydrous dioxane (2 ml) was added ethyl 2-(2,4,5-trifluoro-3-methylbenzoyl)-3-cyclopropylaminoacrylate (300 mg) slowly with stirring. After stirring for 30 minutes at room temperature, to the reacting mixture was added water (5 ml), the resulting precipitate was collected by filtration, washed with water and recrystallized from methanol to give the title compound (220 mg) as white needles.

Workup

  1. stirringAfter stirring for 30 minutes at room temperature, to the reacting mixture
  2. filtrationthe resulting precipitate was collected by filtration
  3. washwashed with water
  4. customrecrystallized from methanol

Sources & evidence

ORD record
ord-095093658f054b148a2624a9d48df6a1
Source dataset
uspto-grants-1990_01
Patent number
US04894458

Reaction notes

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