Ethyl 2-(3-methoxy-4-nitrophenyl)propanoate → Ethyl 2-(4-amino-3-methoxyphenyl)propanoate

HRID 1428750Notes

Reaction equation

HRID 1428750 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:12]([CH3:18])[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:6]=[CH:7][C:8]=1[N+:9]([O-])=O>O1CCCC1.C(O)C.[Pd]>[NH2:9][C:8]1[CH:7]=[CH:6][C:5]([CH:12]([CH3:18])[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:4][C:3]=1[O:2][CH3:1]

Participants

5

Reactant 1

HCID 86679375Ethyl 2-(3-methoxy-4-nitrophenyl)propanoate

Product 1

HCID 86679376Ethyl 2-(4-amino-3-methoxyphenyl)propanoateYield 74.2%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of ethyl 2-(3-methoxy-4-nitrophenyl)propanoate (683 mg, 2.697 mmol) in tetrahydrofuran and ethanol as co-solvent were added 10% Pd/C (70 mg). The mixture was charged with H2 (gas) balloon. The resulting mixture was stirred for 15 h, then filtered using celite. The filtrate removed in vacuo. The crude was purified by column chromatography. Ethyl 2-(4-amino-3-methoxyphenyl)propanoate (447 mg) was obtained as 74% yield.

Workup

  1. additionThe mixture was charged with H2 (gas) balloon
  2. filtrationfiltered
  3. customThe filtrate removed in vacuo
  4. customThe crude was purified by column chromatography

Sources & evidence

ORD record
ord-7b4de9b56e794bddb08196e166bc4583
Source dataset
uspto-grants-2015_01
Patent number
US08937092B2

Reaction notes

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