Cl[C:2](Cl)(Cl)[CH:3]([OH:5])O.[O-]S([O-])(=O)=O.[Na+].[Na+].S(O)(O)(=O)=O.[NH2:20][OH:21].[NH2:22][C:23]1[CH:24]=[C:25]2[C:29](=[CH:30][CH:31]=1)[CH2:28][CH2:27][CH2:26]2.Cl>O>[OH:21][N:20]=[CH:2][C:3]([NH:22][C:23]1[CH:24]=[C:25]2[C:29](=[CH:30][CH:31]=1)[CH2:28][CH2:27][CH2:26]2)=[O:5]To a solution of chloral hydrate (8.34 g, 50.4 mmol) and anhydrous Na2SO4 (43 g, 303 mmol) in water (135 mL) was added a mixture of hydroxylamine sulfate (38.4 g, 234 mmol), 5-aminoindan (6 g, 45 mmol), concentrated HCl (4.71 mL) in water (45 mL). The mixture was heated at 45° C. for 1 h and at 75° C. for 2 h. The reaction mixture was cooled to room temperature. The solid formed was filtered and washed with water. The solid was dried under vacuo to afford 2-hydroxyimino-N-indan-5-yl-acetamide. 1H NMR (500 MHz, DMSO-d6) δ 12.08 (s, 1H); 10.01 (s, 1H); 7.62 (s, 1H); 7.57 (s, 1H); 7.36 (d, J=8.1 Hz, 1H); 7.14 (d, J=8.1 Hz, 1H); 2.83-2.77 (m, 4H); 2.00-1.96 (m, 2H).
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