Ethyl 2-(4-amino-3-nitrophenyl)propanoate → Ethyl 2-(3,4-diaminophenyl)propanoate

HRID 660301Notes

Reaction equation

HRID 660301 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:14])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][C:3]=1[N+:15]([O-])=O>[C].[Pd].C1COCC1.CCO>[NH2:15][C:3]1[CH:4]=[C:5]([CH:8]([CH3:14])[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:6]=[CH:7][C:2]=1[NH2:1]

Participants

4

Reactant 1

HCID 15558027Ethyl 2-(4-amino-3-nitrophenyl)propanoate

Product 1

HCID 12226827Ethyl 2-(3,4-diaminophenyl)propanoate

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

To the flask was added THF/EtOH (1:1, 50 mL) followed by Ethyl 2-(4-amino-3-nitrophenyl)propanoate (2.12 g, 8.90 mmol) and 10% palladium carbon (220 mg) at room temperature. The reaction mixture was hydrogenated and stirred for 3 hrs at 45 psi then filtered through celite bed, and washed with EtOH. The filtrate was concentrated in vacuo. The residue was purified by flash column chromatography on silica gel using EtOAc:hexanes (1:4-1:2) as eluant.

Workup

  1. filtrationthen filtered through celite bed
  2. washwashed with EtOH
  3. concentrationThe filtrate was concentrated in vacuo
  4. customThe residue was purified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-685bce2855ad48f2825085c436acc721
Source dataset
uspto-grants-2011_12
Patent number
US08084484B2

Reaction notes

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