Reacción #1242551

Ecuación de reacción

octahydro-4a-(3-methoxyphenyl)-2-methyl-cis-6(2H)-isoquinolinone ethylene ketal

triethylamine

methyl iodide

dioxane

→

title compound

Octahydro-4a-(3-methoxyphenyl)-2-methyl-cis-6(2H)-isoquinolinone

Disolventes

methanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Concentraciónconcentrated by evaporation
2. 2
   workup.ADDITION100 ml of dioxane and 100 ml of 2 N aqueous hydrochloric acid are added to the residual oil
3. 3
   Extracciónextracted with toluene
4. 4
   ConcentraciónThe extracts are concentrated by evaporation

Procedimiento

25.93 g (0.1 mol) of octahydro-4a-(3-methoxyphenyl)-cis-6(2H)-isoquinolinone (see Example 1), 100 ml of benzene, 11.2 ml (0.2 mol) of ethylene glycol and 8.1 ml (125 mmol) of methanesulphonic acid are boiled for 3 hours in a water separator. The mixture is cooled, made basic with aqueous ammonia and extracted with methylene chloride. The organic phase is evaporated to dryness to yield octahydro-4a-(3-methoxyphenyl)-cis-6(2H)-isoquinolinone ethylene ketal. The ketal is dissolved in 50 ml of absolute methanol, cooled to 0° C., and 13.91 ml (0.1 mol) of triethylamine and 7.46 ml (0.12 mol) of methyl iodide are added thereto. The mixture is kept at 22° for 1 hour. The mixture, containing octahydro-4a-(3-methoxyphenyl)-2-methyl-cis-6(2H)-isoquinolinone ethylene ketal, is mixed with 20 ml of dioxane and concentrated by evaporation. 100 ml of dioxane and 100 ml of 2 N aqueous hydrochloric acid are added to the residual oil. The resultant mixture is stirred for 2 hours at 40°, made basic with aqueous ammonia, and extracted with toluene. The extracts are concentrated by evaporation to yield the title compound as an oil, which is crystallized as the hydrogen fumarate from ethanol.

Fuente