Phosphorus oxychloride → 1-(2-Methylphenyl)-4-chloro-6-methylpyrrolo[3,2-c]quinoline

HRID 1416680Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1416680
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:20]2[C:19]3[CH:18]=[CH:17][CH:16]=[C:15]([CH3:21])[C:14]=3[NH:13][C:12](=O)[C:11]=2[CH:10]=[CH:9]1.P(Cl)(Cl)([Cl:25])=O>>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:20]2[C:19]3[CH:18]=[CH:17][CH:16]=[C:15]([CH3:21])[C:14]=3[N:13]=[C:12]([Cl:25])[C:11]=2[CH:10]=[CH:9]1

Komponenten

3

Edukt 2

HCID 24813Phosphorus oxychlorideHCID 157498281-(2-Methylphenyl)-4-oxo-6-methyl-4,5-dihydropyrrolo[3,2-c]quinoline

Produkt 1

HCID 157498291-(2-Methylphenyl)-4-chloro-6-methylpyrrolo[3,2-c]quinoline

Versuchsvorschrift

1-(2-methylphenyl)-4-oxo-6-methyl-4,5-dihydro pyrrolo[3,2-c]quinoline (1.16 g, 4.0 mmol) was dissolved in 10 ml of phosphoryl chloride (POCl3) and heated for 2 hours. The reaction mixture was stirred at room temperature for 30 minutes after cooling and addition of ice water. The reaction mixture was extracted with methylene chloride (20 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 by silica gel chromatography to obtain 1.12 g of desired compound as an oil in 91% of yield.

Aufarbeitung

  1. temperatureheated for 2 hours
  2. temperatureafter cooling
  3. extractionThe reaction mixture was extracted with methylene chloride (20 ml×3)
  4. washAfter washing with water (15 ml×3)
  5. dry with materialthe organic layer was dried by anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-921f0e052b0e4d37ac4200c333b9eaa4
Quelldatensatz
uspto-grants-1999_06
Patentnummer
US05914402

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