Reaktion #42617

Reaktionsgleichung

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

copper (I) cyanide

→

desired product

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

Lösungsmittel

N-methylpyrrolidinone

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas cooled
2. 2
   Sonstigepartitioned between ethyl acetate and aq. HCl (1N)
3. 3
   TrocknenThe organic layer was dried (magnesium sulfate)
4. 4
   Einengenconcentrated under reduced pressure
5. 5
   Sonstigethe residue was chromatographed on silica gel

Vorschrift

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.

Quelle