Sulfuric Acid → HCID 1115345, compound

Participants

Reaction Conditions

Reaction Steps

3,5-dibromo-6H-anthra[1,9-cd]isoxazol-6-one (1)—Sodium nitrite (993 mg, 14.4 mmol) was added with stirring to conc. H2SO4 (25 mL) at 30-40° C. over 10 min then stirred for an additional 30 min. Next 1-amino-2,4-dibromoanthraquinone (5.0 g, 13.1 mmol) was added over 15 min and the mixture was stirred overnight (16 h) at 50-55° C. The heated solution was poured directly over ice and the resulting yellow precipitate was filtered, washed with cold water, and a 1:1 mixture of ethanol-ether. The moist anthraquinonediazonium hydrogensulfate was added to a solution of NaN3 (1.37 g, 21.0 mmol) in water (25 mL) and stirred overnight (16 h). The light orange solid was filtered off and washed with water followed by a 9:1 mixture of acetone-water. The moist azide was suspended in toluene (40 mL) and heated to 70° C. with stirring. Water and acetone were slowly distilled (using a Dean-Stark apparatus) over a 12 h period. The yellow-orange crystals were filtered and washed with methanol to give 3.78 g (76%) of 3,5-dibromo-6H-anthra[1,9-cd]isoxazol-6-one. 1H NMR (500 MHz, CDCl3) δ 8.44 (d, J=7.8 Hz, 1H), 8.07 (d, J=7.4 Hz, 1H), 7.97 (s, 1H), 7.80 (t, J=7.0 Hz, 1H), 7.71 (t, J=7.4 Hz, 1H). Reference: Sutter, P; Weis, C. D. J. Heterocyclic Chem. 1982, 19, 997-1011.

Provenance & Evidence