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

HRID 2225462Notes

Reaction equation

[CH2:1]([CH:3]1[O:5][CH2:4]1)[Cl:2].[NH2:6][C:7]1[C:20]2[C:19](=[O:21])[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12](=[O:22])[C:11]=2[C:10]([NH2:23])=[CH:9][CH:8]=1>C(O)(=O)C>[Cl:2][CH2:1][CH:3]([OH:5])[CH2:4][NH:6][C:7]1[C:20]2[C:19](=[O:21])[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12](=[O:22])[C:11]=2[C:10]([NH:23][CH2:4][CH:3]([OH:5])[CH2:1][Cl:2])=[CH:9][CH:8]=1

Participants

Conditions

Temperature: 90 °C

Procedure

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.

Workup

customthe solvent was removed under reduced pressure
customThe residue was purified by flash column chromatography (silica gel, CH2Cl2 :MeOH/25:1)
customrecrystallized from CH2Cl2 -Ether-Hexanes

Sources & evidence

ORD record: ord-435db85f85c2480b85c25c154cd3fb3d
Source dataset: uspto-grants-1994_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05344841

Reaction notes

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