Reaktion #9559

Reaktionsgleichung

7-bromo-1-cylcohexylmethyl-2-ethoxymethyl-1H-imidazo[4,5-c]quinoline

3-Chloroperoxybenzoic acid

ammonium hydroxide

p-toluenesulfonyl chloride

→

7-bromo-1-cylcohexylmethyl-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-4-amine

Lösungsmittel

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe crude product was obtained as an oil, which
2. 2
   Sonstigeto form a precipitate
3. 3
   SonstigeThe precipitate was isolated by filtration
4. 4
   Waschenwashed with a small amount of acetonitrile
5. 5
   SonstigeA portion of the brown solid was purified by flash column chromatography on silica gel (
6. 6
   Wascheneluting with chloroform

Vorschrift

The method described in Part J of Example 365 was used to oxidize and aminate 7-bromo-1-cylcohexylmethyl-2-ethoxymethyl-1H-imidazo[4,5-c]quinoline (7.58 g, 22.0 mmol). 3-Chloroperoxybenzoic acid (9.1 g of 50% pure material, 26.4 mmol) was added in five portions during the oxidation step, and the amination with ammonium hydroxide (55 mL) and p-toluenesulfonyl chloride (6.3 g, 33 mmol) proceeded overnight. The crude product was obtained as an oil, which was treated with acetonitrile to form a precipitate. The precipitate was isolated by filtration and washed with a small amount of acetonitrile. A portion of the brown solid was purified by flash column chromatography on silica gel (eluting with chloroform:CMA in a gradient from 95:5 to 85:15) to provide 7-bromo-1-cylcohexylmethyl-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-4-amine as a brown solid, mp 215–216° C.

Quelle