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

HRID 14339

Reaction equation

HRID 14339 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([C:12]([N:14]([CH2:18][CH2:19][CH3:20])[CH2:15][CH2:16][CH3:17])=[O:13])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[Cu][C:22]#[N:23]>CN1CCCC1=O>[C:22]([C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([C:12]([N:14]([CH2:18][CH2:19][CH3:20])[CH2:15][CH2:16][CH3:17])=[O:13])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6])#[N:23]

Participants

4

Reactant 2

HCID 21939662Methyl 3-bromo-5-(dipropylcarbamoyl)benzoateHCID 178418546HCID 178418546, compound

Product 1

HCID 21086168Methyl 3-cyano-5-[(dipropylamino)carbonyl]benzoate

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

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.

Workup

  1. temperaturewas cooled
  2. custompartitioned between ethyl acetate and aq. HCl (1N)
  3. dry with materialThe organic layer was dried (magnesium sulfate)
  4. concentrationconcentrated under reduced pressure
  5. customthe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-1a91c3195d9c448497bee984f21dcaae
Source dataset
uspto-grants-2010_06
Patent number
US07727997B2

Linked notes

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