2-Oxobutanoic Acid → 6-Bromo-3-methyl-7-(methyloxy)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid

HRID 245258

Reaktionsgleichung

Reaktionsgleichung von HRID 245258
[Br: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>[Br: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

5

Edukt 3

HCID 582-Oxobutanoic AcidHCID 679903-(Trifluoromethyl)benzaldehydeHCID 70182544-Bromo-3-methoxyaniline

Produkt 1

HCID 673838286-Bromo-3-methyl-7-(methyloxy)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acidAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of the 4-bromo-3-(methyloxy)aniline (25 g, 124 mmol) and 3-(trifluoromethyl)benzaldehyde (21.54 g, 124 mmol) in ethanol (300 mL) was stirred at reflux for 1 h. 2-Oxobutanoic acid (12.63 g, 124 mmol) was added portionwise. The reaction mixture was stirred at reflux for additional 3 h, warmed to room temperature, and stirred overnight. The solid precipitate was collected by filtration, washed with ethanol, and air dried to give 6-bromo-3-methyl-7-(methyloxy)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid (42.6 g, 78% yield). MS (m/z) 441.0 (M+H+).

Aufarbeitung

  1. temperatureat reflux for 1 h
  2. temperatureat reflux for additional 3 h
  3. stirringstirred overnight
  4. filtrationThe solid precipitate was collected by filtration
  5. washwashed with ethanol, and air
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-7a1d762b8e054e78b76ec2cc34e41965
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08658636B2

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