1,4-Dioxane → HCID 15662876, compound

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Reaction Steps

A mixture of 6-benzyloxy-1-hydroxy-10-methyl-2,3,4,5-tetramethoxy-9-acridone (344 mg, 0.76 mmol) in ethanol (80 ml) containing dioxane (20 ml) and 10% palladium on carbon (200 mg) was hydrogenated at 50 psi for 2.5 hours. The mixture was filtered through a pad of Celite and washed well with ethanol and chloroform. The combined filtrate and washings were evaporated in vacuo to dryness. The solid residue was recrystallized from a mixture of ethanol/hexane (2:3) to give 1,6-Dihydroxy-2,3,4,5-tetramethoxy-9-acridone, 222 mg (80.7%), mp 214-5 ° C. 1H-NMR (DMSO-d6): δ3.69, 3.75, 3.78, 3.80, and 4.02 (each 3H, s, 4×OMe, 1×NMe), 6.94 (1H, d, J=9.0 Hz, H-7), 7.84 (1H, d, J =9.0 Hz, H-8), 10.45 (1H, exchangeable, OH-6), 14.18 (lH, exchangeable, OH-1). Analyses: Calculated for C18H19NO7 : C, 59.83; H, 5.30; N, 3.88. Found C, 60.00, H, 5.38; N, 4.00.

Provenance & Evidence