Ethyl 2-(4-nitrophenyl)propionate → Ethyl 2-(4-aminophenyl)propanoate

HRID 2413910Notes

Reaction equation

HRID 2413910 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]([CH3:16])[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:6][CH:5]=1)([O-])=O>C(O)C.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([CH:10]([CH3:16])[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 3016550Ethyl 2-(4-nitrophenyl)propionate

Product 1

HCID 118009Ethyl 2-(4-aminophenyl)propanoateYield 92.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

48.3 g (0.216 mole) of ethyl 2-(4-nitrophenyl)propionate was dissolved in 400 ml of ethanol and the solution was hydrogenated with 1 g of palladium black catalyst for 6 hours. Palladium black catalyst was filtered out and ethanol was distilled off to give 48.3 g of the remained oily substance. The oily substance was distilled under reduced pressure to give 38.6 g of ethyl 2-(4-aminophenyl)propionate as distillation fraction at 124°-126° C./1-2 mm Hg.

Workup

  1. filtrationPalladium black catalyst was filtered out and ethanol
  2. distillationwas distilled off
  3. customto give 48.3 g of the remained oily substance
  4. distillationThe oily substance was distilled under reduced pressure

Sources & evidence

ORD record
ord-c5e7821c1670432591211e26aa99fcc2
Source dataset
uspto-grants-1988_01
Patent number
US04720506

Reaction notes

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