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

HRID 245239

Reaktionsgleichung

Reaktionsgleichung von HRID 245239
[OH-:1].[K+].[Br:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=[O:13])[C:7]2=O.[F:15][C:16]([F:28])([F:27])[C:17]1[CH:22]=[CH:21][C:20]([C:23](=O)[CH2:24][CH3:25])=[CH:19][CH:18]=1>O.C(O)C>[Br:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:23]([C:20]1[CH:19]=[CH:18][C:17]([C:16]([F:15])([F:27])[F:28])=[CH:22][CH:21]=1)[C:24]([CH3:25])=[C:7]2[C:8]([OH:13])=[O:1]

Komponenten

6

Edukt 3

HCID 68895-BromoisatinHCID 14797Potassium HydroxideHCID 136554p-Trifluoromethylpropiophenone

Produkt 1

HCID 673836206-Bromo-3-methyl-2-[4-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acidAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of potassium hydroxide (13.08 g, 233 mmol) in water (25.2 mL) was added slowly to a solution of 5-bromo-1H-indole-2,3-dione (9.76 g, 38.9 mmol) in ethanol (63.1 mL). 1-[4-(trifluoromethyl)phenyl]-1-propanone (8.64 g, 42.7 mmol) was added and the mixture was heated to reflux for 1 h. The reaction mixture was concentrated to remove the solvent, the residue was dissolved in water, and the mixture was washed three times with Et2O. The aqueous mixture was chilled, and concentrated HCl was added until the solution was pH 3. The solid was collected by filtration, washed with water, and dried under reduced pressure in a water bath at 100° C. The product was obtained as a light brown powder (15.6 g, 98%). This material was used without further purification. MS (m/z) 412.0 (M+H+).

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 1 h
  3. concentrationThe reaction mixture was concentrated
  4. customto remove the solvent
  5. dissolutionthe residue was dissolved in water
  6. washthe mixture was washed three times with Et2O
  7. temperatureThe aqueous mixture was chilled
  8. additionconcentrated HCl was added until the solution
  9. filtrationThe solid was collected by filtration
  10. washwashed with water
  11. customdried under reduced pressure in a water bath at 100° C

Quellen und Nachweise

ORD-Eintrag
ord-cf262dca2b0949e48e17846215830107
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08658636B2

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