Water → HCID 49783914, compound

Participants

Reaction Steps

To an ice cold (0-5° C.) solution of ammonium hydroxide (15 mL) was added a solution of ethyl 3-[(dimethylamino)diazenyl]selenopheno[2,3-b]pyridine-2-carboxylate (150 mg) in THF (5 mL) for 5 min and stirred at rt for 16 h. The solution was poured into ice cooled water and extracted with ethyl acetate (3×100 mL). The combined EtOAc layer was washed with water, brine and dried over sodium sulfate. The solution was filtered and evaporated the solvent. The residue was chromatographed over silica gel column using chloroform-methanol (95:5) as eluents to give the product as a light green color solid, which was recrystallized from chloroform-methanol-hexane (25 mg, 20%), mp 230-232° C. IR (Neat) νmax 3327, 3152, 2913, 1701, 1634, 1360, 1330, 1104, 1058, 1016, 878, 802 cm−1; 1H NMR (400 MHz, DMSO-d6): δ 8.80 (1H, d, J=8.4 Hz, H-4), 8.59 (1H, d, J=3.2 Hz, H-6), 8.18 (1H, s, —CONH2), 7.99 (1H, s, —CONH2), 7.46 (1H, dd, J=8.2, 4.6 Hz, H-5), 3.66 (3H, s, —NCH3), 3.26 (3H, s, —NCH3); 13C NMR (100 MHz, DMSO-d6): δ 164.4, 161.1, 148.3, 142.5, 136.2, 131.5, 130.4, 120.6, 43.6, 36.5; LC-MS (positive ion mode): m/z 318, 320 (M+Na)+.

Provenance & Evidence