Hydrochloric Acid → 2-Amino-5-cyanobenzoic acid

HRID 1372442Notes

Reaction equation

HRID 1372442 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8](Br)=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[Cu](C#N)[C:13]#[N:14].Cl>CN1CCCC1=O.O>[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([C:13]#[N:14])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 798582-Amino-5-bromobenzoic acidHCID 178418260HCID 178418260, compound

Product 1

HCID 100578172-Amino-5-cyanobenzoic acidYield 84.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
190 °C

Procedure

A solution of 2-amino-5-bromobenzoic acid (6.9 g, 31.9 mmol) in N-methyl-2-pyrrolidinone (100 mL) was treated with copper cyanide (4.14 g, 46 mmol) and the mixture was heated at 190° C. for 4.5 hours before being cooled to room temperature and allowed to stand overnight. The mixture was diluted with water (500 mL), acidified with 6N aqueous HCl (100 mL) and extracted with ethyl acetate (6×40 mL). The organic extracts were dried (MgSO4) and concentrated under reduced pressure to yield the crude nitrile (4.35 g, 84%).

Workup

  1. temperaturebefore being cooled to room temperature
  2. extractionextracted with ethyl acetate (6×40 mL)
  3. dry with materialThe organic extracts were dried (MgSO4)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-be6f4032fc2541689c441704ed7eb302
Source dataset
uspto-grants-2007_01
Patent number
US07157585B2

Reaction notes

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