[N+:1]([C:4]1[CH:5]=[C:6]([C:14]([OH:16])=[O:15])[C:7](=[CH:12][CH:13]=1)[CH2:8][C:9]([OH:11])=[O:10])([O-])=O.[H][H].[K+].[Br-]>[OH-].[Na+].[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([C:14]([OH:16])=[O:15])[C:7](=[CH:12][CH:13]=1)[CH2:8][C:9]([OH:11])=[O:10]Compound 13 (15.75 g/0.07 mol) was then dissolved in 150 ml 1N NaOH, treated with 0.55 g of 5% Pd—C and placed in a 500 ml Parr bottle. The resultant mixture was hydrogenated at 47 psi for 3 hours or until the uptake of hydrogen ceased. The solution was suction filtered through Celite, washed with a minimum amount of DI water and then acidified with c. HCl to pH 4-5. The solution was stored in the refrigerator (scratch to induce crystallization) over night. The product crystallized and was isolated by suction filtration. A second and third crop can be obtained by allowing the filtrate to slowly concentrate at room temperature. The product formed: 11 g (81% yield). 1H NMR (d6-DMSO): δ 7.13 (s, 1H), 6.91 (d, J=8 Hz, 1H), 6.64 (d, J=8 Hz, 1H), 3.69 (s, 2H); IR (KBr): 3320-3640 (br), 1700 (s), 1550 (s) cm−1; EI-MS (m/z) 194.1 (M−); MS/MS 150; Anal. Calcd. for C9H9NO4.(H2O)0.25: C, 54.13; H, 4.80; N, 7.02%. Found: C, 54.09; H, 5.26; N, 7.01; Na, 0.29%.
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