Hydrochloric Acid → HCID 59547213, compound

To a solution of methyl 5-methyl-4-nitroselenophene-2-carboxylate (2.3 g, 9.28 mmol) in a mixture of water (5 mL) and methanol (40 mL) was added conc. hydrochloric acid (1.0 mL). To the above solution was added iron powder (2.6 g, 46.4 mmol) followed by ammonium chloride (2.5 g, 46.4 mmol) at rt. The reaction mixture was refluxed for 1 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 (4×100 mL) and the combined organic layer was dried over sodium sulfate and filtered. Solvent was evaporated and the residue was chromatographed over silica gel column using hexane-ethyl acetate (80:20) as eluent to give methyl 4-amino-5-methylselenophene-2-carboxylate (1.6 g, 79%), mp 66-68° C. 1H NMR (400 MHz, DMSO-d6): δ 7.57 (1H, s, H-3), 4.72 (2H, br s, —NH2), 3.73 (3H, s, —COOCH3), 2.24 (3H, s, —CH3).

1. temperatureThe reaction mixture was refluxed for 1 h
2. filtrationThe solution was filtered
3. extractionThe solution was extracted with ethyl acetate (4×100 mL)
4. dry with materialthe combined organic layer was dried over sodium sulfate
5. filtrationfiltered
6. customSolvent was evaporated
7. customthe residue was chromatographed over silica gel column

ORD record

ord-101a07ee0b0149b1bdcbe8ef49e8d7da

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08143237B2