Hydrochloric Acid → 6-Bromo-3-methyl-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid

HRID 245144

Reaktionsgleichung

Reaktionsgleichung von HRID 245144
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=O.[OH-:13].[K+].[F:15][C:16]([F:28])([F:27])[C:17]1[CH:18]=[C:19]([C:23](=O)[CH2:24][CH3:25])[CH:20]=[CH:21][CH:22]=1.Cl>C(O)C.O.CCO.O>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]=[C:23]([C:19]1[CH:20]=[CH:21][CH:22]=[C:17]([C:16]([F:15])([F:27])[F:28])[CH:18]=1)[C:24]([CH3:25])=[C:5]2[C:6]([OH:11])=[O:13]

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 68895-BromoisatinHCID 14797Potassium HydroxideHCID 137064Propiophenone, 3'-(trifluoromethyl)

Produkt 1

HCID 673839956-Bromo-3-methyl-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acidAusbeute 87,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 19096565Water ethanolLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

5-Bromoisatin (198 g, 788 mmol) was dissolved in ethanol (1.2 L) in a 6 L conical jacketed lab reactor equipped with a mechanical stirrer and an internal temperature probe. A solution of KOH (265 g, 4730 mmol) in water (0.480 L) was added slowly via addition funnel over ca. 1 hour, such that the vessel temperature was maintained at 20° C. 1-[3-(Trifluoromethyl)phenyl]-1-propanone (159 g, 788 mmol) was added in one portion and the reactor was heated to reflux for 1 h. The reaction mixture was cooled to 20° C. and acidified to pH˜2 by addition of 450 mL of concentrated HCl. An additional 1.5 L of 50% EtOH/H2O was added to facilitate filtration. The slurry was filtered and the filter cake was rinsed twice with 1 L portions of 50% EtOH/water. The solid was dried in vacuo to give 6-bromo-3-methyl-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid (281.7 g, 87% yield) as a fine off-white solid. MS (m/z) 412.7 (M+H+).

Aufarbeitung

  1. customequipped with a mechanical stirrer
  2. temperaturethe reactor was heated
  3. temperatureto reflux for 1 h
  4. temperatureThe reaction mixture was cooled to 20° C.
  5. filtrationfiltration
  6. filtrationThe slurry was filtered
  7. washthe filter cake was rinsed twice with 1 L portions of 50% EtOH/water
  8. customThe solid was dried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-45b06bc08fc74b0da5c9182f1b0d29db
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08658636B2

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