Ammonium Chloride → HCID 57625530, compound

Participants

Reaction Steps

A solution of 1-(3-methyl-4-nitrophenyl)-4-(4-(trifluoromethyl)phenyl)pyridin-2(1H)-one (0.46 g, 1.2 mmol) in 9:1 EtOH/H2O (20 mL) was treated with iron powder (0.62 g, 11.1 mmol) and NH4Cl (33 mg, 0.61 mmol), and the resulting suspension was heated at reflux for 18 h. The reaction mixture was filtered, while hot, through Celite® with portions of CH2Cl2 (2×25 mL) and MeOH (2×25 mL). The filtrates were combined and made basic with 1 N NaOH (10 mL). The solution was extracted with CH2Cl2 (2×40 mL) and the combined organic extracts were dried over Na2SO4, filtered and concentrated to provide the title compound (0.409 g, 100%) as a yellow solid: 1H NMR (500 MHz, DMSO-d6) δ 7.97 (d, J=8.0 Hz, 2H), 7.85 (d, J=8.5 Hz, 2H), 7.68 (d, J=7.0 Hz, 1H), 6.96 (s, 1H), 6.92 (dd, J=8.5, 2.0 Hz, 1H), 6.80 (d, J=1.5 Hz, 1H), 6.67 (d, J=8.0 Hz, 1H), 6.63 (dd, J=7.0, 2.0 Hz, 1H), 5.11 (s, 2H), 2.09 (s, 3H).

Provenance & Evidence