Potassium Carbonate → 3-(2,6-Dichloro-4-nitro-phenoxy)-quinoline-8-carboxylic acid methyl ester

HRID 1819770Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1819770
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:14]=1[N:13]=[CH:12][C:11]([OH:15])=[CH:10]2)=[O:4].[Cl:16][C:17]1[CH:18]=[C:19]([N+:25]([O-:27])=[O:26])[CH:20]=[C:21]([Cl:24])[C:22]=1Cl.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:14]=1[N:13]=[CH:12][C:11]([O:15][C:22]1[C:21]([Cl:24])=[CH:20][C:19]([N+:25]([O-:27])=[O:26])=[CH:18][C:17]=1[Cl:16])=[CH:10]2)=[O:4]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 883653,4,5-TrichloronitrobenzeneHCID 57440941Methyl 3-hydroxyquinoline-8-carboxylate

Produkt 1

HCID 574409423-(2,6-Dichloro-4-nitro-phenoxy)-quinoline-8-carboxylic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

To a solution of 3-Hydroxy-8-quinolinecarboxylic acid methyl ester (97) (256 mg, 1.26 mmol) and 3,4,5-trichloronitrobenzene (294 mg, 1.30 mmol) in acetone (40 mL) was added K2CO3 (870 mg, 6.30 mmol). This mixture was refluxed for 3.5 h. The reaction mixture was cooled to room temperature and insoluble materials were removed by Celite filtration. The filtrate was concentrated and the residue was purified by column chromatography. (hexane/AcOEt=4/1, 80 g of silica gel) to afford compound 98. 1H NMR (300 MHz, DMSO-d6) δ 3.92 (3H, s), 7.67 (1H, dd, J=7.3 Hz), 7.79 (1H, d, J=2.9 Hz), 7.88 (1H, dd, J=1.5, 7.3 Hz), 9.05 (1H, d, J=2.9 Hz).

Aufarbeitung

  1. temperatureThis mixture was refluxed for 3.5 h
  2. custominsoluble materials were removed by Celite filtration
  3. concentrationThe filtrate was concentrated
  4. customthe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-b27e6c942dec411d8819b6390271a6d8
Quelldatensatz
uspto-grants-2009_10
Patentnummer
US07601841B2

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