Hydrochloric Acid → HCID 49783990, compound

Participants

Reaction Steps

To a solution of ethyl 3-[(dimethylamino)diazenyl]selenopheno[2,3-b]pyridine-2-carboxylate (170 mg, 0.52 mmol), prepared as described in Example 6 step b) in methanol (10 mL) was added a solution of sodium hydroxide (83 mg, 2.08 mmol) in water (2 mL) and stirred at room temperature (rt) for 2 h. The mixture was diluted with ice cold water and acidified with dil. HCl. The mixture was stirred for 30 min and extracted with ethyl acetate (3×100 mL). The combined organic 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, which was recrystallized from chloroform-methanol-hexane as a light brown color solid (30 mg, 20%), mp 172-174° C. IR (KBr) νmax 3427, 3025, 2919, 1707, 1265, 1218, 1013, 863 cm−1; 1H NMR (400 MHz, DMSO-d6): δ 13.09 (1H, br s, —COOH), 8.65-8.69 (2H, m, H-4,6), 7.53 (1H, dd, J=8.2, 4.6 Hz, H-5), 3.67 (3H, s, —NCH3), 3.29 (3H, s, —NCH3); LC-MS (positive ion mode): m/z 319, 321 (M+Na)+.

Provenance & Evidence