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

HRID 371320Notes

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]

Participants

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

temperatureThe reaction mixture is cooled to room temperature
customthe precipitated crystals are separated by filtration
washwashed with ethanol
customThe crude crystals thus obtained
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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