Réaction #42617

Équation de réaction

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

copper (I) cyanide

→

desired product

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

Solvants

N-methylpyrrolidinone

Conditions de réaction

Traitement

1. 1
   Températurewas cooled
2. 2
   Autrepartitioned between ethyl acetate and aq. HCl (1N)
3. 3
   SéchageThe organic layer was dried (magnesium sulfate)
4. 4
   Concentrationconcentrated under reduced pressure
5. 5
   Autrethe residue was chromatographed on silica gel

Mode opératoire

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.

Source