Sodium Hydroxide → 1,4-Bis{[(oxiran-2-yl)methyl]amino}anthracene-9,10-dione

HRID 847410Notes

Reaction equation

HRID 847410 reaction equation
Cl[CH2:2][CH:3]([OH:28])[CH2:4][NH:5][C:6]1[C:19]2[C:18](=[O:20])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11](=[O:21])[C:10]=2[C:9]([NH:22][CH2:23][CH:24]([OH:27])[CH2:25]Cl)=[CH:8][CH:7]=1.[OH-].[Na+]>CO>[O:27]1[CH2:25][CH:24]1[CH2:23][NH:22][C:9]1[C:10]2[C:11](=[O:21])[C:12]3[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:18](=[O:20])[C:19]=2[C:6]([NH:5][CH2:4][CH:3]2[O:28][CH2:2]2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 1218099,10-Anthracenedione, 1,4-bis((3-chloro-2-hydroxypropyl)amino)-

Product 1

HCID 1002141,4-Bis{[(oxiran-2-yl)methyl]amino}anthracene-9,10-dioneYield 89.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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.

Workup

  1. customthe solvent was removed under reduced pressure
  2. customThe residual solid was then purified by flash column chromatography (silica gel, CH2Cl2 : MeOH/25:1)
  3. customRecrystalization from CH2Cl2

Sources & evidence

ORD record
ord-004e709ccb5049d986eb3505ec3a8e67
Source dataset
uspto-grants-1992_08
Patent number
US05141957

Reaction notes

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