Dimethyl 2-[(4-nitrophenyl)methyl]propanedioate → 3-(4-Aminophenyl)-2-carbomethoxypropanoic acid methyl ester
Reaction equation
[CH3:1][O:2][C:3](=[O:19])[CH:4]([C:15]([O:17][CH3:18])=[O:16])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[CH:8][CH:7]=1.[H][H]>C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:19])[CH:4]([C:15]([O:17][CH3:18])=[O:16])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([NH2:12])=[CH:8][CH:7]=1Participants
Procedure
The compound 2-carbomethoxy-3-(4-nitrophenyl)propanoic acid methyl ester (p-nitrobenzylmalonate dimethyl ester) (2.00 g, 7.55 mmole) was dissolved in 70 mL of ethyl acetate containing 5 percent palladium on carbon (1.0 g; Aldrich Chemical Company) catalyst and was hydrogenated in a Parr shaker employing 50 psig of hydrogen at 22° C. Hydrogen uptake was rapid (15 minutes) and the mixture was maintained under hydrogen pressure for another 3 hrs. The pressure vessel was vented and flushed with nitrogen (N2). The suspension was filtered through a pad of celite and the solvent was removed in vacuo using a rotary evaporator to provide 3-(4-aminophenyl)-2-carbomethoxypropanoic acid methyl ester (p-aminobenzylmalonate dimethyl ester) (1.76 g, 7.41 mmole) as a light yellow oil in 98 percent yield. The structure was confirmed by 1H nuclear magnetic resonance (PMR) and 13C nuclear magnetic resonance (CMR) as well as mass spectroscopy (MS) spectral analysis.
Workup
- customat 22° C
- custom(15 minutes)
- temperaturethe mixture was maintained under hydrogen pressure for another 3 hrs
- customflushed with nitrogen (N2)
- filtrationThe suspension was filtered through a pad of celite
- customthe solvent was removed in vacuo
- customa rotary evaporator
Sources & evidence
- ORD record
- ord-c15e1e179c9847d5b9392c31f00de141
- Source dataset
- uspto-grants-1993_12
- Patent number
- US05274119
Reaction notes
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