4-Cyanophenylacetic acid → 4-Aminomethylphenylacetic acid

HRID 1372440Notes

Reaction equation

HRID 1372440 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([OH:12])=[O:11])=[CH:5][CH:4]=1)#[N:2]>O.N.[Ni]>[NH2:2][CH2:1][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([OH:12])=[O:11])=[CH:5][CH:4]=1

Participants

5

Reactant 1

HCID 795874-Cyanophenylacetic acid

Product 1

HCID 15141444-Aminomethylphenylacetic acidYield 101.5%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 222AmmoniaSolventHCID 962WaterSolvent

Procedure

A solution of 4-cyanophenylacetic acid (12.11 g, 0.075 mol) in water (163 mL) and concentrated aqueous ammonia (40 mL) was stirred at room temperature and Raney nickel (6.3 g) was added. The resulting suspension was stuirred under a hydrogen atmosphere for 24 hours before the reaction mixture was filtered through celite and evaporated in vacuo to give crude 4-(aminomethyl)-phenylacetic acid (12.57 g; 100%) as a pale blue solid.

Workup

  1. filtrationwas filtered through celite
  2. customevaporated in vacuo

Sources & evidence

ORD record
ord-8d631778be7e48d7b244041b86700b86
Source dataset
uspto-grants-2007_01
Patent number
US07157585B2

Reaction notes

Loading…