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Benzoyl chloride → 1-methyl-2-phenyl-1H-imidazo[4,5-c]quinoline

HRID 981907
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 981907
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[NH:12][CH3:13])=[CH:9][CH:8]=[CH:7][CH:6]=2.[C:14](Cl)(=O)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O.N>N1C=CC=CC=1.O>[CH3:13][N:12]1[C:11]2[C:10]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[N:4]=[CH:3][C:2]=2[N:1]=[C:14]1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 7412Benzoyl chlorideHCID 12896473Azane;hydrateHCID 139583463-Amino-4-(methylamino)quinoline

Produkt 1

HCID 100381871-methyl-2-phenyl-1H-imidazo[4,5-c]quinoline

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 1049Pyridine
Lösungsmittel

Versuchsvorschrift

2.1 g (0.012 mole) of crude product of 3-amino-4-methylaminoquinoline was dissolved in 20 ml of pyridine, and 1.5 ml (0.013 mole) of benzoyl chloride was added followed by stirring at room temperature for one hour. The reaction solution was concentrated under reduced pressure, and 20 ml of phosphorus oxychloride was added to the concentrate, followed by refluxing with heating for 3 hours. The residues obtained by concentration under reduced pressure were dissolved in water and the solution was made alkaline with ammonia water. The precipitate was collected by filtration, washed with water and purified by silica gel column chromatography (eluting solvent: chloform/methanol=30/1), to afford 2.1 g of Compound a.

Aufarbeitung

  1. concentrationThe reaction solution was concentrated under reduced pressure, and 20 ml of phosphorus oxychloride
  2. additionwas added to the concentrate
  3. temperatureby refluxing
  4. temperaturewith heating for 3 hours
  5. customThe residues obtained by concentration under reduced pressure
  6. filtrationThe precipitate was collected by filtration
  7. washwashed with water
  8. custompurified by silica gel column chromatography (eluting solvent: chloform/methanol=30/1)

Quellen und Nachweise

ORD-Eintrag
ord-1fd4e3b96b9c466a83b50ae38bd80e07
Quelldatensatz
uspto-grants-1991_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04994468

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