4-Cyanobenzoic acid → 4-(Aminomethyl)Benzoic Acid

HRID 1174503Notes

Reaction equation

HRID 1174503 reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1)#[N:2]>[Ni].CO>[NH2:2][CH2:1][C:3]1[CH:4]=[CH:5][C:6]([C:7]([OH:9])=[O:8])=[CH:10][CH:11]=1

Participants

4

Reactant 1

HCID 120874-Cyanobenzoic acid

Product 1

HCID 655264-(Aminomethyl)Benzoic AcidYield 84%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A mixture of 4-cyano benzoic acid (500 g, 3.4 mol) and Raney Nickel (100 g) in methanol (5 L) was hydrogenated at a pressure of 10 kg for 16 h. The catalyst was removed by filtration, followed by the removal of the solvent under reduced pressure to afford 4-(aminomethyl)benzoic acid (430 g, 84%) as a white solid.

Workup

  1. customThe catalyst was removed by filtration
  2. customfollowed by the removal of the solvent under reduced pressure

Sources & evidence

ORD record
ord-31f052c1aed34fb788e3e3dd05bcd70e
Source dataset
uspto-grants-2010_11
Patent number
US07838522B2

Reaction notes

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