[C:1]([O:4][C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([N+:16]([O-])=O)[C:13]=1[O:14][CH3:15])[C:8]([OH:10])=[O:9])(=[O:3])[CH3:2].Cl.[H][H]>C(O)C.CO.[Pd]>[C:1]([O:4][C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([NH2:16])[C:13]=1[O:14][CH3:15])[C:8]([OH:10])=[O:9])(=[O:3])[CH3:2]3-Acetoxy-4-methoxy-5-nitro-benzoic acid (4.50 g, 17.6 mmol) (R. T. Borchardt et al., J. Med. Chem. 25 (1982), 312-323; F. Tiemann et al., Ber. dt. Chem. Ges. 9 (1876), 937) was dissolved in ethanol (180 ml) and 0.5 M hydrogen chloride in methanol (4 ml) and hydrogenated in an H-Cube™ hydrogenation reactor with 100 bar hydrogen at 40° C. over a 10% palladium on charcoal cartridge. The mixture was evaporated to dryness to give 4.1 g of the title compound.
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