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

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Reaction Steps

To a solution of 1,4-Bis-(3-chloro-2-hydroxylpropylamino)-9, 10-anthracenedione (8.3 g, 19.8 mmoles) in MeOH (500 mL) at 60° C. was added NaOH (3.5 g). 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). Recrystalization from CH2Cl2 :hexanes yielded the title compound 1,4-Bis-(2,3-epoxypropylamino)-9, 10-anthracenedione, (6.2 g, 89.37%), mp 189°-190° C.: 1H NMR (CDCl3) δ 2.74 (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