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2-Methoxyaniline → HCID 57990632, Verbindung

HRID 1968466
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1968466
Cl[CH2:2][C:3]1[C:12]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][O:21][CH3:22])=[CH:15][C:14]=2[O:23][CH3:24])=[CH:11][CH:10]=[C:9]2[C:4]=1[C:5]([CH3:27])=[CH:6][C:7]([CH3:26])([CH3:25])[NH:8]2.[CH3:28][O:29][C:30]1[CH:36]=[CH:35][CH:34]=[CH:33][C:31]=1[NH2:32].C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C)C=O.O>[CH3:24][O:23][C:14]1[CH:15]=[C:16]([O:19][CH2:20][O:21][CH3:22])[CH:17]=[CH:18][C:13]=1[C:12]1[C:3]([CH2:2][NH:32][C:31]2[CH:33]=[CH:34][CH:35]=[CH:36][C:30]=2[O:29][CH3:28])=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([CH3:25])([CH3:26])[CH:6]=[C:5]2[CH3:27]
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Komponenten

7

Edukt 4

HCID 70002-MethoxyanilineHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 579906385-Chloromethyl-6-(2-methoxy-4-methoxymethoxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinoline

Produkt 1

HCID 57990632HCID 57990632, VerbindungAusbeute 61,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962
Water
Lösungsmittel
HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 5-chloromethyl-6-(2-methoxy-4-methoxymethoxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinoline (Reference Compound No. 2, 262 mg, 0.675 mmol), 2-methoxyaniline (84 μL, 0.74 mmol) and potassium carbonate (151 mg, 1.09 mmol) was suspended in anhydrous N,N-dimethylformamide (4 mL) and the suspension was stirred at 80° C. overnight. After cooling down, ethyl acetate (20 mL) and water (20 mL) were added to the reaction mixture and separated. The organic layer was washed with saturated brine (20 mL), dried over anhydrous magnesium sulfate, and then the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give the titled reference compound (196 mg) as a yellow amorphous product. (Yield 61%)

Aufarbeitung

  1. temperatureAfter cooling down
  2. customseparated
  3. washThe organic layer was washed with saturated brine (20 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was removed under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-8163e02eea1a4038bd6bcbe87f260d0c
Quelldatensatz
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08426406B2

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