Sodium Nitrite → HCID 58015549, compound

Participants

Reaction Steps

A solution of 5-(4-amino-3-methylphenyl)-2-(3-chlorophenyl)furo[3,2-c]pyridine-4(5H)-one (1.02 g, 2.91 mmol) in AcOH (23 mL) was treated with a solution of NaNO2 (0.20 g, 2.9 mmol) in H2O (0.65 mL). After stirring at ambient temperature for 12 h, the reaction mixture was concentrated. The resulting solid was partitioned in CH2Cl2 and water. Any solids were removed by filtration. The filtrate was extracted with CH2Cl2 (4×30 mL). The organics were dried (Na2SO4), filtered, recombined with the removed solids and concentrated. Purification by flash chromatography (silica gel, CH2Cl2/MeOH, 100:0 to 90:10) gave the title compound (0.409 g, 40%) as a tan solid: 1H NMR (300 MHz, DMSO-d6) δ 13.29 (s, 1H), 8.17 (m, 1H), 7.96 (t, J=1.8 Hz, 1H), 7.87-7.83 (m, 2H), 7.73-7.71 (m, 2H), 7.65 (d, J=8.7 Hz, 1H), 7.52 (t, J=8.1 Hz, 1H), 7.46-7.43 (m, 1H), 7.38 (dd, J=9.0, 2.1 Hz, 1H), 6.89 (d, J=7.8 Hz, 1H).

Provenance & Evidence