HCID 67191235, compound → 2,3-Diamino-5-(5-methyl-3-oxo-4-pyridin-2-ylmethyl-cyclohexa-1,5-dienyl)-benzoic acid methyl ester
Reaction equation
[CH3:1][O:2][C:3](=[O:29])[C:4]1[CH:9]=[C:8]([C:10]2[CH:15]=[C:14]([CH3:16])[CH:13]([CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=3)[C:12](=[O:24])[CH:11]=2)[CH:7]=[C:6]([N+:25]([O-])=O)[C:5]=1[NH2:28]>[Pd].C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:29])[C:4]1[CH:9]=[C:8]([C:10]2[CH:15]=[C:14]([CH3:16])[CH:13]([CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=3)[C:12](=[O:24])[CH:11]=2)[CH:7]=[C:6]([NH2:25])[C:5]=1[NH2:28]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
To a slurry of 10% palladium on carbon (0.045 g) in ethyl acetate (20 mL) was added 2-amino-5-(5-methyl-3-oxo-4-pyridin-2-ylmethyl-cyclohexa-1,5-dienyl)-3-nitro-benzoic acid methyl ester (0.176 g, 0.44 mmol). The resulting mixture was hydrogenated at 30 psi for 24 hours. The reaction was filtered, concentrated in vacuo, and the crude isolate purified (SiO2, 2 to 10% methanol in methylene chloride) to afford the title compound. 1H NMR (500 MHz, CDCl3) δ 2.5 (s, 3H), 3.99 (s, 3H), 5.3 (s, 2H), 5.38 (bs, 2H), 6.39 (s, 1H), 6.25 (s, 1H), 7.93-7.21 (m, 4H), 8.61 (s, 1H), 8.93 (s, 1H).