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Imidazole → 3-Quinolinecarboxylic acid, 1,4-dihydro-6,8-difluoro-1-ethyl-7-(1H-imidazoly-1-yl)-4-oxo-

HRID 371320
Notes
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Reaction equation

HRID 371320 reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:15])=[C:10](F)[C:11]=2[F:13])[C:6](=[O:16])[C:5]([C:17]([OH:19])=[O:18])=[CH:4]1)[CH3:2].[NH:20]1[CH:24]=[CH:23][N:22]=[CH:21]1>CN(C)C=O>[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:15])=[C:10]([N:20]3[CH:24]=[CH:23][N:22]=[CH:21]3)[C:11]=2[F:13])[C:6](=[O:16])[C:5]([C:17]([OH:19])=[O:18])=[CH:4]1)[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 795ImidazoleHCID 98351791-Ethyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Product 1

HCID 30221173-Quinolinecarboxylic acid, 1,4-dihydro-6,8-difluoro-1-ethyl-7-(1H-imidazoly-1-yl)-4-oxo-Yield 48.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To 1-ethyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (13.6 g) and imidazole (10.2 g) is added dimethylformamide (80 ml), and the mixture is stirred at 100° C. for 1.25 hour. The reaction mixture is cooled to room temperature, and the precipitated crystals are separated by filtration and washed with ethanol. The crude crystals thus obtained are recrystallized from dimethylformaide to give the title compound (7.7 g) as colorless needles. Melting point: 283°-288° C. (decomp. with foam), being gradually colored from about 245° C. IR (KBr, νC=O): near 1720 cm-1.

Workup

  1. temperatureThe reaction mixture is cooled to room temperature
  2. customthe precipitated crystals are separated by filtration
  3. washwashed with ethanol
  4. customThe crude crystals thus obtained
  5. customare recrystallized from dimethylformaide

Sources & evidence

ORD record
ord-6b8a391377b64b17ba34267eeec97abc
Source dataset
uspto-grants-1985_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04530930

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes