Water → 2-[4-(Aminomethyl)phenyl]benzonitrile

HRID 494349Notes

Reaction equation

HRID 494349 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=2[C:11]#[N:12])=[CH:5][CH:4]=1.C1(=O)[NH:21]C(=O)C2=CC=CC=C12.[K].O.O.NN>CN(C=O)C.CO>[NH2:21][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=2[C:11]#[N:12])=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 15019124'-(Bromomethyl)-2-cyanobiphenylHCID 24194345Phthalimide potassium salt

Product 1

HCID 13933412-[4-(Aminomethyl)phenyl]benzonitrileYield 154.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 2-(4-bromomethylphenyl)benzonitrile (12 g) and potassium phtalimide (15 g) in DMF (200 ml) was stirred at 70° C. for 5 hours. After addition of water, the mixture was extracted with methylene chloride. The extract was washed with water, dried and concentrated to dryness to give crystals. Recrystallization from ethyl acetate-isopropyl ether gave colorless crystals. To a suspension of the crystals in methanol (500 ml) was added hydrazine hydrate (10 ml) and the mixture was refluxed for 12 hours. After evaporation of the solvent, the residue was dissolved in ethyl acetate and the solution was washed with 1N-NaOH and water. The organic layer was dried and concentrated to dryness to give crystals (14.2 g, 93%).

Workup

  1. extractionthe mixture was extracted with methylene chloride
  2. washThe extract was washed with water
  3. customdried
  4. concentrationconcentrated to dryness
  5. customto give crystals
  6. customRecrystallization from ethyl acetate-isopropyl ether
  7. customgave colorless crystals
  8. temperaturethe mixture was refluxed for 12 hours
  9. customAfter evaporation of the solvent
  10. dissolutionthe residue was dissolved in ethyl acetate
  11. washthe solution was washed with 1N-NaOH and water
  12. customThe organic layer was dried
  13. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-9a6b3c4aae1047d3845755c65b4f1c2b
Source dataset
uspto-grants-2009_05
Patent number
US07538133B2

Reaction notes

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