Ethyl 4-nitrophenylacetate → p-Aminophenylacetic acid ethyl ester

HRID 1858210Notes

Reaction equation

HRID 1858210 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[CH:8][CH:7]=1)[CH3:2]>CO.[Pd]>[NH2:12][C:9]1[CH:8]=[CH:7][C:6]([CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:15])=[CH:11][CH:10]=1

Participants

4

Reactant 1

HCID 79517Ethyl 4-nitrophenylacetate

Product 1

HCID 225219p-Aminophenylacetic acid ethyl esterYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 1 g (4.78 mmol) of ethyl-4-nitrophenylacetate in 10 ml of dry methanol was treated with 100 mg of 10% palladium-on-carbon and then hydrogenated at room temperature and at atmospheric pressure for 4 hours. The catalyst was removed by filtration and the filtrate was evaporated to give 830 mg (97%) of ethyl 4-aminophenylacetate as a mobile yellow oil.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-1a4d09d5df4e4119b99bf453c0674d03
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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