Hydrochloric Acid → HCID 59547204, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl and methyl esters of 3-amino-4,5,6,7-tetrahydrobenzo[2,1-d]selenophene-2-carboxylate (400 mg, 1.54 mmol), conc. HCl (0.6 mL, 6.17 mmol) in water (3.5 mL) and acetone (3 mL) was added sodium nitrite (120 mg, 1.69 mmol) in portions for 5 min at 0° C. After stirring at 0-5° C. for 1 h, the reaction mixture was added to the solution of potassium carbonate (800 mg, 5.85 mmol) and dimethylamine (0.62 mL, 40%, 5.54 mmol) in water (4.3 mL) at 0° C. The mixture was stirred at 0-5° C. for 1 h and poured into ice cold water. The solution was extracted with chloroform (3×200 mL) and 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 hexane-EtOAc (95:5) as eluents to give the product as brown oil (200 mg, 50%). It is a mixture of ethyl and methyl mixtures. 1H NMR (400 MHz, CDCl3): δ 3.74 (3H, s, —COOCH3), 3.34 (6H, br s, —N(CH3)2), 2.79 (2H, br s, H-4), 2.41 (2H, br s, H-7), 1.74-1.82 (4H, m, H-5,6); LC-MS (positive ion mode): m/z 336, 338 (M+Na)±.

Provenance & Evidence