Methyl p-nitrophenylacetate → Methyl 2-(4-aminophenyl)acetate

HRID 1807243Notes

Reaction equation

HRID 1807243 reaction equation
[CH3:1][O:2][C:3](=[O:14])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-])=O)=[CH:7][CH:6]=1.[H][H]>CO.CCOC(C)=O.[Pd]>[CH3:1][O:2][C:3](=[O:14])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[CH:7][CH:6]=1

Participants

6

Reactant 2

HCID 270191Methyl p-nitrophenylacetateHCID 178418361HCID 178418361, compound

Product 1

HCID 2761030Methyl 2-(4-aminophenyl)acetateYield 98.7%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

(4-Nitro-phenyl)-acetic acid methyl ester (1.08 g, 5.52 mmol) was dissolved in methanol (50 mL) and EtOAc (50 mL), then added to a Parr bottle containing 10% Pd/C (0.42 g), the vessel was subjected to hydrogen atmosphere (40 psi) for 2 h under the Parr Shaker Apparatus conditions. Workup with filtration via a glass membrane filter paper, solvent was removed under reduced pressure to afford (4-amino-phenyl)-acetic acid methyl ester as an oil (0.9 g, 98.7%). 1H NMR (CDCl3) δ 7.05 (d, 1H), 6.62 (d, 1H), 3.63 (s, 3H), 3.6 (bs, 2H) 3.5 (s, 2H).

Workup

  1. filtrationWorkup with filtration via a glass membrane
  2. filtrationfilter paper, solvent
  3. customwas removed under reduced pressure

Sources & evidence

ORD record
ord-a8e9686215ad4ab582860b39363dd6f3
Source dataset
uspto-grants-2013_01
Patent number
US08354444B2

Reaction notes

Loading…