4-amino-3-nitrophenylPropanoic acid → 2-(3,4-Diaminophenyl)propanoic acid
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
Product 1
Reagents, catalysts & solvents 2
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
- filtrationthen filtered through celite bed
- washwashed with EtOH
- concentrationThe filtrate was concentrated in vacuo
- customThe residue was purified by flash column chromatography on silica gel
Sources & evidence
- ORD record
- ord-a5989e60d4724b3885b90cfe40673cb4
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08785474B2
Reaction notes
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