[CH3:1][O:2][C:3]([C:5]1[Se:9][C:8]([C:10]([O:12][CH3:13])=[O:11])=[C:7]([N+:14]([O-])=O)[CH:6]=1)=[O:4].Cl.[Cl-].[NH4+]>O.CO.[Fe]>[CH3:13][O:12][C:10]([C:8]1[Se:9][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:6][C:7]=1[NH2:14])=[O:11]To a solution of methyl 5-(methoxycarbonyl)-3-nitroselenophene-2-carboxylate (8.0 g, 27.3 mmol) in a mixture of water (20 mL) and methanol (150 mL) was added conc. hydrochloric acid (2.75 mL, 27.3 mmol). To the above solution was added iron powder (7.64 g, 136.5 mmol) followed by ammonium chloride (7.3 g, 136.5 mmol) at rt. The reaction mixture was refluxed for 3 h and was then allowed to cool to rt. The solution was filtered and basified with saturated sodium bicarbonate solution. The solution was extracted with ethyl acetate (4×200 mL) and the combined organic layer was washed with brine, dried over sodium sulfate and filtered. Solvent was evaporated and the residue was chromatographed over silica gel column using hexane-ethyl acetate (95:5) as eluent to give the product as pale yellow color solid (5.8 g, 41%), mp 144-146° C. IR (neat) vmax. 3449, 3339, 1673, 1604, 1556, 1285, 1217, 1125, 1023 cm−1; 1H NMR (400 MHz, CDCl3): δ 7.55 (1H, s, H-4), 5.57 (2H, s, —NH2), 3.86 (3H, s, —COOCH3), 3.82 (3H, s, —COOCH3); LC-MS (negative ion mode): m/z 264, 262 (M−H)−.
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