Methanol → HCID 178422436, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 6-(4-bromo-2-methylphenylamino)-5-nitropyridin-2-ol (4.50 g, 13.9 mmol) in MeOH (30 mL) was added Raney Ni (1.00 g). The mixture was stirred vigorously under H2 atmosphere overnight at which time additional Raney nickel (500 mg) was added. After stirring for an additional 45 h under H2 atmosphere, the mixture was filtered through Celite® and concentrated. The residue was dissolved in THF (20 mL) and trimethoxymethane (25 mL) and trifluoroacetic acid (100 μL) was added. The mixture was heated at 50° C. for 12 h followed by additional heating at 80° C. for 4 h. After cooling to room temperature, the solution was concentrated in vacuo. The residue was purified by HPLC to give the title compound as a white solid (442 mg). LCMS m/z=304.1 [M+H]+; 1H NMR (400 MHz, CDCl3) δ ppm 2.07 (s, 3H), 6.61 (d, J=8.6 Hz, 1H), 7.15 (d, J=8.3 Hz, 1H), 7.48 (dd, J1=8.3, J2=1.9 Hz, 1H), 7.55 (s, 1H), 7.82 (s, 1H), 8.04 (d, J=8.6 Hz, 1H).

Provenance & Evidence