Reacción #339659

Ecuación de reacción

dodecyl bromide

NaI

NaH

8-hydroxyl-quinoline-2-carboxylic acid methyl ester

→

8-dodecyloxy-quinoline-2-carboxylic acid methyl ester

Rendimiento 14.0%

Disolventes

DMF

DCM

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothe red reaction
2. 2
   OtroThe crude material resulting from removal of solvents by rotary evaporation
3. 3
   Lavadowashed with water
4. 4
   Secadodried over Na2SO4
5. 5
   Filtraciónfiltered
6. 6
   OtroThe resulting solution was evaporated to dryness

Procedimiento

In a first step, dodecyl bromide (767 μL, 3.2 mmol), NaI (478 mg, 3.2 mmol) and NaH (76 mg, 3.2 mmol) were added to a solution of 8-hydroxyl-quinoline-2-carboxylic acid methyl ester (2.11 mmol) stirring in DMF (dry, 10 mL), and the red reaction was allowed to stir overnight. The crude material resulting from removal of solvents by rotary evaporation was taken into DCM, washed with water, dried over Na2SO4, and filtered. The resulting solution was evaporated to dryness and the desired intermediate, 8-dodecyloxy-quinoline-2-carboxylic acid methyl ester, was obtained by HPLC (isocratic, 75% acetonitrile, 25% water) yielding 169 mg (about 14% yield). This intermediate was in turn deprotected using LiOH in THF/H2O as described in the method of Example 336 to yield the title compound, which was utilized further without additional purification or characterization.

Fuente