2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 2-n-Butyl-5-methoxy-6-(4-chlorophenyl)-4,5-dihydro-1,2,4-triazin-3-one

Participants

Reaction Steps

2-n-Butyl-6-(4-chlorophenyl)-4,5-dihydro-1,2,4-triazin-3-one (2.16 g, 8.13 mmol), and DDQ (1.94 g, 8.5 mmol in 80 mL of ethyl acetate were stirred at room temperature overnight, then refluxed for 3 hours. The reaction mixture was cooled, washed twice with aqueous potassium carbonate solution, washed with brine, dried over magnesium sulfate and stripped. The product was dissolved in 15 mL of ethyl acetate and 15 mL of methanol. Alumina (7 g) was added, and the slurry was stirred for 3 hours at room temperature. The slurry was filtered, and the filtrate was stripped. The product was chromatographed on an alumina column to give 0.97 g of of 2-n-butyl-5-methoxy-6-(4-chlorophenyl)-4,5-dihydro-1,2,4-triazin-3-one (Compound 3).

Provenance & Evidence