تفاعل #42617

معادلة التفاعل

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

copper (I) cyanide

→

desired product

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

المذيبات

N-methylpyrrolidinone

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةwas cooled
2. 2
   أخرىpartitioned between ethyl acetate and aq. HCl (1N)
3. 3
   تجفيفThe organic layer was dried (magnesium sulfate)
4. 4
   تركيزconcentrated under reduced pressure
5. 5
   أخرىthe residue was chromatographed on silica gel

الإجراء التجريبي

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.

المصدر