4-amino-3-nitrophenylPropanoic acid → 2-(3,4-Diaminophenyl)propanoic acid

HRID 660305Notes

Reaction equation

HRID 660305 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:12])[C:9]([OH:11])=[O:10])=[CH:4][C:3]=1[N+:13]([O-])=O>[C].[Pd].CCO.O>[NH2:13][C:3]1[CH:4]=[C:5]([CH:8]([CH3:12])[C:9]([OH:11])=[O:10])[CH:6]=[CH:7][C:2]=1[NH2:1]

Participants

4

Reactant 1

HCID 122268174-amino-3-nitrophenylPropanoic acid

Product 1

HCID 122268182-(3,4-Diaminophenyl)propanoic acid

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 19096565Water ethanolSolvent

Procedure

To the flask was added EtOH/H2O (3.5:1, 45 mL) followed by 2-(4-Amino-3-nitro-phenyl)-propionic acid (5.73 g, 27.3 mmol) and 10% palladium carbon (117 mg) at room temperature. The reaction mixture was hydrogenated and stirred for 5 hrs at 64 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 CH2Cl2:MeOH (10:1) 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-357a73832591471fa79c948b01639105
Source dataset
uspto-grants-2011_12
Patent number
US08084484B2

Reaction notes

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