3-Phenylbenzaldehyde → 3-(Aminomethyl)biphenyl

HRID 1264684Notes

Reaction equation

HRID 1264684 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 SN 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 SN 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-e9ea6fffce5a47bbbbb87d824e2008c5
Source dataset
uspto-grants-2003_04
Patent number
US06544978B2

Reaction notes

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