Ethyl 2-(4-cyanophenyl)acetate → Ethyl [4-(aminomethyl)phenyl]acetate

HRID 1374733Notes

Reaction equation

HRID 1374733 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:5][CH:4]=1)#[N:2]>N.[Ni]>[NH2:2][CH2:1][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:5][CH:4]=1

Participants

4

Reactant 1

HCID 279718Ethyl 2-(4-cyanophenyl)acetate

Product 1

HCID 11535728Ethyl [4-(aminomethyl)phenyl]acetate

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 222AmmoniaSolvent

Procedure

0.5 g (2.6 mmol) of ethyl (4-cyanophenyl)acetate was dissolved in 70 ml of ethanolic ammonia solution and hydrogenated, at room temperature and under standard pressure, over Raney nickel. After 45 minutes, the mixture was filtered and evaporated. This resulted in 0.42 g (82%) of ethyl (4-aminomethylphenyl)acetate. MS (ES+): m/e=194.11

Workup

  1. filtrationthe mixture was filtered
  2. customevaporated
  3. customThis resulted in 0.42 g (82%) of ethyl (4-aminomethylphenyl)acetate

Sources & evidence

ORD record
ord-c29348e54dc74efa97f6cfaf37f94093
Source dataset
uspto-grants-2007_01
Patent number
US07166609B2

Reaction notes

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