Reaktionsgleichung
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[O:9][CH3:10].[F:11][C:12]([F:22])([F:21])[C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH:16]=O.O=[C:24]([CH2:28][CH3:29])[C:25]([OH:27])=[O:26]>C(O)C>[F:1][C:2]1[CH:8]=[C:7]2[C:5](=[CH:4][C:3]=1[O:9][CH3:10])[N:6]=[C:16]([C:15]1[CH:18]=[CH:19][CH:20]=[C:13]([C:12]([F:22])([F:21])[F:11])[CH:14]=1)[C:28]([CH3:29])=[C:24]2[C:25]([OH:27])=[O:26]Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
A solution of 4-fluoro-3-(methyloxy)aniline (13.6 g, 96 mmol) and 3-(trifluoromethyl)benzaldehyde (16.78 g, 96 mmol) in ethanol (200 mL) was heated to reflux for 1 h. 2-Oxobutanoic acid (9.84 g, 96 mmol) was added portionwise. The reaction mixture was stirred at reflux for an additional 3 h, cooled to room temperature, and stirred overnight. The solid was collected by filtration, washed with ethanol, and air dried to afford 6-fluoro-3-methyl-7-(methyloxy)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid (17.9 g, 49% yield). 1H NMR (400 MHz, DMSO-d6)™ 14.34 (br. s., 1H), 7.93-7.98 (m, 2H), 7.88 (d, J=7.78 Hz, 1H), 7.77 (t, J=7.65 Hz, 1H), 7.71 (d, J=8.53 Hz, 1H), 7.54 (d, J=12.05 Hz, 1H), 4.03 (s, 3H), 2.38 (s, 3H); MS (m/z) 380.1 (M+H+).
Aufarbeitung
- temperatureto reflux for 1 h
- temperatureat reflux for an additional 3 h
- stirringstirred overnight
- filtrationThe solid was collected by filtration
- washwashed with ethanol, and air
- customdried
Quellen und Nachweise
- ORD-Eintrag
- ord-c3737da9472248bc8d7a7fb69787410b
- Quelldatensatz
- uspto-grants-2014_02
- Patentnummer
- US08658636B2
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