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2-Methoxyaniline → 1-(2-Methoxyphenyl)-4-oxo-6-methyl-2,3,4,5-tetrahydropyrrolo[3,2-c]quinoline

HRID 1416668
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1416668
[O:1]=[C:2]1[CH:11]2[CH2:12][CH2:13]O[C:10]2=[C:9]2[C:4]([C:5]([CH3:15])=[CH:6][CH:7]=[CH:8]2)=[N:3]1.[CH3:16][O:17][C:18]1[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=1[NH2:20]>C(O)COCCO.O>[CH3:16][O:17][C:18]1[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=1[N:20]1[C:10]2[C:9]3[CH:8]=[CH:7][CH:6]=[C:5]([CH3:15])[C:4]=3[NH:3][C:2](=[O:1])[C:11]=2[CH2:12][CH2:13]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 70002-MethoxyanilineHCID 676261834-Oxo-6-methyl-2,3-dihydrofuro[3,2-c]quinoline

Produkt 1

HCID 536616231-(2-Methoxyphenyl)-4-oxo-6-methyl-2,3,4,5-tetrahydropyrrolo[3,2-c]quinolineAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8117Diethylene GlycolLösungsmittel

Reaktionsbedingungen

Temperatur
250 °C

Versuchsvorschrift

4-Oxo-6-methyl-2,3-dihydrofuro[3,2-c]quinoline (201 mg, 1.0 mmol) was dissolved in 10 ml of diethylene glycol and 2-methoxyaniline (282 μl, 2.5 mmol) was added under nitrogen. The reaction mixture was heated at 250° C. for 15 hours. The reaction mixture was diluted with 20 ml of salt water and the aqueous layer was extracted with methylene chloride (15 ml×3). After washing with water (15 ml×3), the organic layer was dried by anhydrous magnesium sulfate and filtered, and concentrated under reduced pressure. The residue was purified with ethyl acetate as eluent by silica gel chromatography to obtain 242 mg of desired compound as solid in 79% of yield.

Aufarbeitung

  1. extractionthe aqueous layer was extracted with methylene chloride (15 ml×3)
  2. washAfter washing with water (15 ml×3)
  3. dry with materialthe organic layer was dried by anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified with ethyl acetate as eluent by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-b6ce27e180f746d39bb752e84363ea78
Quelldatensatz
uspto-grants-1999_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05914402

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