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

HRID 1626840Notes

Reaction equation

HRID 1626840 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-eefa10ec95e84a21b8e62c59ff103696
Source dataset
uspto-grants-2014_07
Patent number
US08785474B2

Reaction notes

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