Hydrochloric Acid → HCID 67183740, compound

Temperature

2.5 °C

To a solution of methyl 4-aminothiophene-3-carboxylate (200 mg, 1.27 mmol) and cone. HCl (0.5 mL, 5.09 mmol) in H2O (5 mL) was added NaNO2 (96 mg, 1.39 mmol) in portions for 5 min at 0° C. After stirring for 0.5 h at 0-5° C., the reaction mixture was added to the solution of K2CO3 (665 mg, 4.8 mmol) and dimethylamine (0.5 mL, 40%, 4.57 mmol) in H2O (5 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 (3×30 mL). The combined CHCl3 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 (90:10) as eluents to give the product as pale red color oil (20 mg, 8%). 1H NMR (400 MHz, CDCl3): δ 8.00 (1H, d, J=2.8 Hz), 6.97 (1H, d, J=3.6 Hz), 3.85 (3H, s), 3.34 (6H, br s).

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 (3×30 mL)
4. washThe combined CHCl3 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-2be28bae742f463ebe1f90f00839ac40

Source dataset

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08258119B2