Hydrochloric Acid → HCID 59547204, compound

Temperature

2.5 °C

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)±.

1. stirringThe mixture was stirred at 0-5° C. for 1 h
2. additionpoured into ice cold water
3. extractionThe solution was extracted with chloroform (3×200 mL)
4. washthe combined organic layer was washed with water, brine
5. dry with materialdried over sodium sulfate
6. filtrationThe solution was filtered
7. customevaporated the solvent
8. customThe residue was chromatographed over silica gel column

ORD record

ord-05b3fb11e80e420d8508429ae7fa3235

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08143237B2