Ammonia → 4-(1-Aminoethyl)benzoic acid

HRID 2413766Notes

Reaction equation

HRID 2413766 reaction equation
[C:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=1)(=O)[CH3:2].[NH3:13]>[Ni]>[NH2:13][CH:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=1)[CH3:2]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 114704-Acetylbenzoic Acid

Product 1

HCID 125682714-(1-Aminoethyl)benzoic acid

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

4-Acetylbenzoic acid (4.1 g) is dissolved in 50 mL ammonia-saturated methanol. Raney nickel catalyst (1.5 g; activity grade III) is then added and the mixture reduced under hydrogen atmosphere (4750 psi) at 80° C. for 17 hrs. After removal of the catalyst by suction filtration, the filtrate is evaporated and the residue dissolved in H2O. The solution is passed through a 2.5×15 cm column of Dowex 50X8-400 resin (H+ form) and eluted with 1N NH4OH. Evaporation of the eluate leaves a residue (2.9 g) which is recrystallized from H2O/acetone and characterized as 4-(1-aminoethyl)benzoic acid, m.p. >300° C.

Workup

  1. customat 80° C.
  2. customfor 17 hrs
  3. customAfter removal of the catalyst
  4. filtrationby suction filtration
  5. customthe filtrate is evaporated
  6. dissolutionthe residue dissolved in H2O
  7. washeluted with 1N NH4OH
  8. customEvaporation of the eluate

Sources & evidence

ORD record
ord-5ae085b4852e4658bdb446f9090b24ea
Source dataset
uspto-grants-1988_01
Patent number
US04719233

Reaction notes

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