Nitric Acid → 1-(2-methylpropyl)-8-nitro-1H-imidazo[4,5-c]quinolin-4-amine

HRID 9472

Reaktionsgleichung

Reaktionsgleichung von HRID 9472
[CH3:1][CH:2]([CH3:18])[CH2:3][N:4]1[C:16]2[C:15]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[N:9]=[C:8]([NH2:17])[C:7]=2[N:6]=[CH:5]1.[N+:19]([O-])([OH:21])=[O:20].[OH-].[NH4+]>S(=O)(=O)(O)O>[CH3:1][CH:2]([CH3:18])[CH2:3][N:4]1[C:16]2[C:15]3[CH:14]=[C:13]([N+:19]([O-:21])=[O:20])[CH:12]=[CH:11][C:10]=3[N:9]=[C:8]([NH2:17])[C:7]=2[N:6]=[CH:5]1

Komponenten

5

Edukt 3

HCID 944Nitric AcidHCID 14923Ammonium HydroxideHCID 57469Imiquimod

Produkt 1

HCID 114490011-(2-methylpropyl)-8-nitro-1H-imidazo[4,5-c]quinolin-4-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1118Sulfuric AcidLösungsmittel2×

Versuchsvorschrift

A solution of 1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine (28.3 g, 0.118 mol) in concentrated sulfuric acid (150 mL) was cooled to 5° C. A solution of 70% nitric acid (8.4 mL, 0.130 mol) in sulfuric acid (30 mL) was added in portions over a period of one hour. The reaction temperature was maintained below 10° C. The solution was allowed to warm to ambient temperature, stirred for two hours, and then poured into 500 g of ice. The resulting solution was made basic with the addition of ammonium hydroxide while keeping the solution cold. A precipitate formed, was isolated by filtration, washed with water, and dried to provide 1-(2-methylpropyl)-8-nitro-1H-imidazo[4,5-c]quinolin-4-amine as a yellow solid.

Aufarbeitung

  1. temperatureThe reaction temperature was maintained below 10° C
  2. customA precipitate formed
  3. customwas isolated by filtration
  4. washwashed with water
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-364907e077a64b9c904a0cc083c30353
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091214B2

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