Water → 4-chloro-1-(3-chloropropyl)-1H-imidazo[4,5-c]quinolin-2-ol

HRID 388612

Reaktionsgleichung

Reaktionsgleichung von HRID 388612
O(Cl)[Cl:2].[P+3].[Cl:5][C:6]1[C:15]2[N:16]=[C:17]([OH:23])[N:18]([CH2:19][CH2:20][CH2:21]O)[C:14]=2[C:13]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[N:7]=1.O>CN(C=O)C>[Cl:5][C:6]1[C:15]2[N:16]=[C:17]([OH:23])[N:18]([CH2:19][CH2:20][CH2:21][Cl:2])[C:14]=2[C:13]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[N:7]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 178479710HCID 178479710, Verbindung2×HCID 1785208234-chloro-1-(3-hydroxypropyl)-1H-imidazo[4,5-c]quinolin-2-ol

Produkt 1

HCID 1785173254-chloro-1-(3-chloropropyl)-1H-imidazo[4,5-c]quinolin-2-olAusbeute 64,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Phosphorus(III) oxychloride (7.9 g, 52 mmol) was added dropwise to a stirred solution of 4-chloro-1-(3-hydroxypropyl)-1H-imidazo[4,5-c]quinolin-2-ol (12 g, 43 mmol) in DMF (150 mL), and the reaction was stirred overnight at room temperature. An analysis by LC/MS indicated the presence of starting material, and additional phosphorus(III) oxychloride (7.9 g) was added. The reaction was stirred overnight at room temperature and then cooled to approximately 0° C. Water (300 mL) was slowly added, and a precipitate formed. The mixture was stirred for several minutes, and the precipitate was isolated by filtration, washed with water and diethyl ether, and dried in a vacuum oven to provide 8.2 g of 4-chloro-1-(3-chloropropyl)-1H-imidazo[4,5-c]quinolin-2-ol.

Aufarbeitung

  1. additionwas added
  2. stirringThe reaction was stirred overnight at room temperature
  3. temperaturecooled to approximately 0° C
  4. customa precipitate formed
  5. stirringThe mixture was stirred for several minutes
  6. customthe precipitate was isolated by filtration
  7. washwashed with water and diethyl ether
  8. customdried in a vacuum oven

Quellen und Nachweise

ORD-Eintrag
ord-b2f346afa2eb4a70a4d0655d1eb603b8
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08377957B2

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