3-Phenylbenzaldehyde → 3-(Aminomethyl)biphenyl

HRID 413831Notes

Reaction equation

HRID 413831 reaction equation
[C:1]1([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]=O)[CH:2]=1.[NH3:15].CO>CO>[C:9]1([C:1]2[CH:2]=[C:3]([CH:4]=[CH:5][CH:6]=2)[CH2:7][NH2:15])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 1210533-PhenylbenzaldehydeHCID 21705897Ammonia methanol

Product 1

HCID 27603683-(Aminomethyl)biphenyl

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 3-biphenylcarboxaldehyde (0.011 eq.) in 30 mL of methanol was added 10 eq. of 7N NH3/MeOH and NaCNBH4 (2 eq.). A yellow gum precipitated from solution. The solution was then heated at 60° C. until gum dissolved and the solution was stirred at room temperature overnight. The reaction mixture was then concentrated and the resulting residue diluted with ice water and ethyl acetate. The organic layer was then washed with brine and extracted with 5N HCl. The pH of the aqueous layer was then adjusted to 12 and the aqueous layer was extracted with cold ethyl acetate. The organic layer was dried over Na2SO4, filtered and concentrated to give 3-(phenyl)benzyl amine as an oil.

Workup

  1. customA yellow gum precipitated from solution
  2. dissolutiondissolved
  3. concentrationThe reaction mixture was then concentrated
  4. additionthe resulting residue diluted with ice water and ethyl acetate
  5. washThe organic layer was then washed with brine
  6. extractionextracted with 5N HCl
  7. extractionthe aqueous layer was extracted with cold ethyl acetate
  8. dry with materialThe organic layer was dried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-2362a3d82e5f468f8d56ef4f79594f7e
Source dataset
uspto-grants-2003_05
Patent number
US06569851B1

Reaction notes

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