C([O-])(=O)C.[NH4+].[N+:6]([C:9]1[C:24]([C:25](=[O:27])[CH3:26])=[CH:23][C:12]2[O:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][O:22][C:11]=2[CH:10]=1)([O-])=O.C1(C)C=CC=CC=1>[Fe].O>[NH2:6][C:9]1[C:24]([C:25](=[O:27])[CH3:26])=[CH:23][C:12]2[O:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][O:22][C:11]=2[CH:10]=1A Mixture of iron powder (477 mmol, 27 g), ammonium acetate (500 mmol, 31 g), 1-(3-Nitro-6,7,9,10,12,13-hexahydro-5,8,11,14-tetraoxa-benzocyclododecen-2-yl)-ethanone (120 mmol, 36 g), toluene (500 ml) and water (500 ml) was refluxed overnight, or until completion. The mixture was filtered through celite and washed with EtOAc. The organic layer was washed with water and Sat. NaCl, dried over Na2SO4, and concentrated to afford the product, 90%. 1HNMR (400 MHz, DMSO) δ 7.82 (s, 1H), 7.61 (s, 1H), 5.45 (s, 2H), 4.35 (s, 4H), 3.87 (d, 4H), 3.62 (s, 4H), 2.71 (s, 3H). LC/MS Calcd for (M+H)+282.3. found 282.5.
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