Epichlorohydrin → 9,10-Anthracenedione, 1,4-bis((3-chloro-2-hydroxypropyl)amino)-

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Reaction Conditions

Reaction Steps

Epichlorohydrin (84.5 mL, 1.08 mol) was added to a solution of 1,4 -diaminoanthraquinone (Aldrich Chemical Company, Milwaukee, Wis.) (10 g, 42 mmol) in glacial acetic acid (200 mL) at room temperature. The solution was stirred for 30 minutes at 90° C. and the solvent was removed under reduced pressure. The residue was purified by flash column chromatography (silica gel, CH2Cl2 :MeOH/25:1) and recrystallized from CH2Cl2 -Ether-Hexanes to give a pure blue solid of the title compound (12.46 g, 70%), mp 167°-169° C.: 1H NMR (CDCl3) δ3.21 (broad, 2H, OH) , 3.5-3.6 (m, 6H, CHCH2), 3.75 (d, J=3 Hz, 4H, CH2), 4.19 (broad, 2H, NH), 7.03 (d, J=3.2 Hz, 2H, ArH (2, 3)), 7.69 (m, 2H, ArH (6, 7)), 8.27 (m, 2H, ArH (5, 8)). Anal. Calcd for C20H20O4N2Cl2 ×0.25 H2O: C, 56.15; H, 4.83; N, 6.55. Found: C, 56.18; H, 4.76; N, 6.29.

Provenance & Evidence