Реакция #42617

Уравнение реакции

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

copper (I) cyanide

→

desired product

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

Растворители

N-methylpyrrolidinone

Условия реакции

Обработка

1. 1
   Температураwas cooled
2. 2
   Другоеpartitioned between ethyl acetate and aq. HCl (1N)
3. 3
   СушкаThe organic layer was dried (magnesium sulfate)
4. 4
   Концентрированиеconcentrated under reduced pressure
5. 5
   Другоеthe residue was chromatographed on silica gel

Методика

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.

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