Ethyl (3-nitrophenyl)acetate → Ethyl 2-(3-aminophenyl)acetate

HRID 2056637Notes

Reaction equation

HRID 2056637 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:7]=[CH:8][CH:9]=1)([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 14997011Ethyl (3-nitrophenyl)acetate

Product 1

HCID 13042040Ethyl 2-(3-aminophenyl)acetateYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Thus obtained ethyl 3-nitrophenylacetate (5.0 g, 24 mmol) was then dissolved in methanol (80 mL) together with 10 wt % of palladium/carbon (150 mg), and stirred under a hydrogen atmosphere (1 kg/cm2) for 14 hours. The reaction solution was filtered through Celite so as to remove the palladium/carbon catalyst, evaporated under reduced pressure so as to remove the solvent, and the residue was purified through silica gel column chromatography (hexane:ethyl acetate (v/v)=7:3) to thereby obtain a purified ethyl 3-aminophenylacetate (yield: 4.0 g, yield ratio: 100%) as a syrup.

Workup

  1. filtrationThe reaction solution was filtered through Celite so as
  2. customto remove the palladium/carbon catalyst
  3. customevaporated under reduced pressure so as
  4. customto remove the solvent
  5. customthe residue was purified through silica gel column chromatography (hexane:ethyl acetate (v/v)=7:3)

Sources & evidence

ORD record
ord-9445b79a0ebb492b906dcf85b2d9ad31
Source dataset
uspto-grants-2008_02
Patent number
US07335673B2

Reaction notes

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