Reacción #42617

Ecuación de reacción

Methyl 3-bromo-5-[(dipropylamino)carbonyl]benzoate

copper (I) cyanide

→

desired product

methyl 3-cyano-5-[(dipropylamino)carbonyl]benzoate

Disolventes

N-methylpyrrolidinone

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawas cooled
2. 2
   Otropartitioned between ethyl acetate and aq. HCl (1N)
3. 3
   SecadoThe organic layer was dried (magnesium sulfate)
4. 4
   Concentraciónconcentrated under reduced pressure
5. 5
   Otrothe residue was chromatographed on silica gel

Procedimiento

Methyl 3-bromo-5-[(dipropylamino)carbonyl]benzoate (Preparation 3) (0.15 g), copper (I) cyanide, and N-methylpyrrolidinone (1 mL) was heated at 150° C. overnight, at which time the mixture was cooled and partitioned between ethyl acetate and aq. HCl (1N). The organic layer was dried (magnesium sulfate), concentrated under reduced pressure, and the residue was chromatographed on silica gel using ethyl acetate-hexane (20/80) to give 0.066 g of the desired product. ms (m+H) 289.2. See also preparation 7 for the preparation of the acid.

Fuente