1H-1,2,4-Triazole → HCID 22459731, compound

Participants

Reaction Conditions

Reaction Steps

2-Chloro-5-nitroanisole (0.5 g, 2.67 mmol), potassium hydroxide (219 mg, 3.92 mmol) and 1,2,4-triazole (736 mg, 10.66 mmol) were dissolved in dimethyl sulfoxide (2.5 mL), and heated at 110° C. for 24 h. The reaction mixture was poured onto ice-water (100 mL). The solid was collected by filtration and purified by flash column chromatography CH3Cl 2% methanol to yield 110 mg of 3-Methoxy-4-(1H-1,2,4-triazol-1-yl)nitrobenzene. 3-Methoxy-4-(1H-1,2,4-triazol-1-yl)nitrobenzene (105 mg, 0.48 mmol) was dissolved in methanol (10 mL) and 10% palladium on carbon (20 mg) was added. The reaction mixture was hydrogenated at 45 psi overnight. The catalyst was removed by filtration and the solvent evaporated to yield 77 mg of 265A. HPLC method A 97% pure. Mass spectrum M+H+=191.1, 1H 400 MHz NMR (CH3OD): δ8.65 (s, 1H), 8.09 (s, 1H), 7.25 (d, 1H, J=8.56), 6.52 (d, 1H, J=2.19) 6.40-6.35 (m, 1H), 3.83 (s, 3H).

Provenance & Evidence