[N+:1]([C:4]1[CH:14]=[CH:13][C:7]([CH:8]=[CH:9][C:10]([OH:12])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].S(O)(O)(=O)=O.NO.NOS(O)(=O)=O.[OH-].[Na+]>O>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[CH:13][CH:14]=1)([O-:3])=[O:2]A suspension of 4-nitrocinnamic acid (13.5 g, 70 mmol) in H2O (100 mL) was treated with hydroxylamine sulfate (18.5 g, 113 mmol) and hydroxylamine-o-sulfonic acid (43.5 g, 385 mmol) at 0° C. The pH was adjusted to 7.6 with 50% NaOH, and additional base was added as needed over the next 6 hours to maintain a pH of 7.6. The mixture was then filtered, and the filtrate was acidified to pH 2 with 2N H2SO4. The solids that formed were filtered, washed with H2O, and recrystallized from EtOH:H2O(30 mL: 150 mL) to give the title compound. 1H NMR (CDCl3) δ 2.71 (t, 2 H), 3.03 (t, 2 H), 7.34 (d, 2 H), 8.13 (d, 2 H).
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