Reacción #2079781

Ecuación de reacción

1-[3-(aminooxy)propyl]-2-propyl-1H-imidazo[4,5-c]quinolin-4-amine

Acetone

→

acetone O-[3-(4-amino-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)propyl]oxime

Rendimiento 87.5%

Disolventes

methanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawas heated until the starting material
2. 2
   workup.DISSOLUTIONdissolved
3. 3
   ConcentraciónThe reaction was then concentrated under reduced pressure
4. 4
   Otrothe residue (800 mg) was purified by column chromatography on silica gel (25 g
5. 5
   Lavadoeluting sequentially with 98:2 dichloromethane

Procedimiento

A mixture of 1-[3-(aminooxy)propyl]-2-propyl-1H-imidazo[4,5-c]quinolin-4-amine (prepared as described in Example 1, 0.605 g, 2.02 mmol) in methanol was heated until the starting material dissolved. Acetone (3 mL, 40 mmol) was then added, and the resulting solution was stirred for two hours. The reaction was then concentrated under reduced pressure, and the residue (800 mg) was purified by column chromatography on silica gel (25 g, eluting sequentially with 98:2 dichloromethane:methanol and 95:5 dichloromethane:methanol) to provide 600 mg of acetone O-[3-(4-amino-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)propyl]oxime as a beige powder, mp 147-150° C.

Fuente