Sodium Hydroxide → 1,4-Bis(2,3-epoxypropylamino)-9,10-anthracenedione

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Reaction Steps

Sodium hydroxide (3.5 g) was added to a solution of 1,4-bis-(3-chloro-2-hydroxypropylamino)-9, 10-anthracenedione (8.3 g, 19.8 mmoles), the compound of Example 1, in MeOH (500 mL) at 60° C. The resulting blue solution was stirred at room temperature for 4 hours, and the solvent was removed under reduced pressure. The residual solid was then purified by flash column chromatography (silica gel, CH2Cl2 : MeOH/25:1). Recrystallization from CH2Cl2 : hexanes yielded the title compound 1,4-bis-(2, 3-epoxypropylamino)-9, 10-anthracenedione which is compound 3 in Scheme 2 (6.2 g, 89.37%), mp 189°-190° C.: 1H NMR (CDCl3) δ2.74 (m, 1H, CH2), 2.87 (m, 1H, CH2), 3.26 (m, 1H, CH), 3.57 (m, 1H CH2), 3.78 (m, 1H, CH2), 7.32 (s, 2H, Ar (2,3)), 7.71 (dd, J=3.2 Hz, 5.5 Hz, 2H, Ar (6, 7)), 8.34 (dd, J=3.2 Hz, 5.5 Hz, 2H, Ar (5, 8)), 10.76 (s, 2H, NH). Anal. Calcd for C20H18O4N2 ×0.25 H2O: C, 67.66; H, 5.25; N, 7.93. Found: C, 67.72; H, 5.55; N, 7.54. IR: 3400, 3070, 2910, 1640, 1220, 900.

Provenance & Evidence