Hydrochloric Acid → HCID 178526707, compound

Participants

Reaction Conditions

Reaction Steps

2,6-Dichloro-3-nitropyridine (2.0 g, 10.4 mmol) and 2,3-difluoroaniline (2.5 g, 20.7 mmol) were taken up in ethanol (10.0 mL) and heated to 120° C. for 18 hours in a sealed tube. The solution was cooled in an ice bath, and the resulting precipitate was collected by vacuum filtration. The solid intermediate was dissolved in dioxane (12 mL) and 2 M aqueous potassium hydroxide solution (6.0 mL, 12.0 mmol) was added. The reaction mixture was heated to 80° C. for 18 h. After cooling to ambient temperature the mixture was diluted with EtOAc and H2O. The organic phase was discarded and the aqueous phase was acidified with 1 N HCl and extracted with EtOAc (2×). The organics were washed with brine, dried over MgSO4, filtered, and concentrated to give the title compound (743 mg). 1H NMR (400 MHz, CDCl3) δ ppm 6.52 (d, J=9.2 Hz, 1H), 6.80 (m, 1H), 6.97 (q, J=8.2 Hz, 1H), 7.06 (d, J=8.1 Hz, 1H), 8.22 (d, J=9.2 Hz, 1H), 10.09 (s, 1H).

Provenance & Evidence