1,2-Benzenedicarboxylic acid, 3-nitro-, 1,2-dimethyl ester → Dimethyl 3-aminobenzene-1,2-dicarboxylate
Reaction equation
[CH3:1][O:2][C:3](=[O:17])[C:4]1[C:5](=[C:10]([N+:14]([O-])=O)[CH:11]=[CH:12][CH:13]=1)[C:6]([O:8][CH3:9])=[O:7]>CO.[Pd]>[CH3:1][O:2][C:3](=[O:17])[C:4]1[C:5](=[C:10]([NH2:14])[CH:11]=[CH:12][CH:13]=1)[C:6]([O:8][CH3:9])=[O:7]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
The compound 2 (205 g, 1.0 mol) was dissolved in 2 L of MeOH. Catalytic 10% Pd/C was added and the solution was hydrogenated under H2 (45 psi) on a Parr hydrogenation apparatus at room temperature overnight. Filtered through celite and evaporated to give a quantitative yield of 3-amino-phthalic acid dimethyl ester, 3. 1H NMR (300 MHz, DMSO-d6): 7.26 (t, J=7.33 Hz, 1H), 6.94 (d, J=8.34 Hz, 1H), 6.77 (d, J=8.33 Hz, 1H), 6.12 (s, 2H), 3.77 (s, 3H), 3.76 (s, 3H). 13C NMR: 51.51, 51.77, 110.50, 115.16, 118.56, 131.26, 133.16, 148.28, 167.12, 168.11.