Peracetic Acid → 2-Chloroquinoxaline-1-oxide

Participants

Reaction Steps

1 gram mole of quinoxaline (130 g.) is oxidized by treatment with 3150 milliliters of a 1.2 molar solution of peracetic acid in acetic anhydride, according to the method of Landquist, reported in the Journal of the Chemical Society at page 2816 (1953). The product, quinoxaline-1,4-dioxide, having a melting point of between 241.5° and 242.0°C. (with decomposition), is obtained in 50-60% yield. It is reacted with 530 grams of benzenesulfonyl chloride at a temperature of 25°C. for 1 to 12 hours and the resulting grey-green solid product is treated with 440 milliliters of a 10% aqueous solution of sodium bicarbonate, to produce 2-chloroquinoxaline-1-oxide. The product obtained has a melting point of 115°-116°C. after crystallization from cyclohexane or methanol. It is obtained in approximately 60% yield. The method for this reaction is reported in the Journal of General Chemistry, V.S.S.R., volume 34, page 2836 (1964 ).

Provenance & Evidence