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

HRID 2225463Notes

Reaction equation

HRID 2225463 reaction equation
[OH-].[Na+].Cl[CH2:4][CH:5]([OH:30])[CH2:6][NH:7][C:8]1[C:21]2[C:20](=[O:22])[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13](=[O:23])[C:12]=2[C:11]([NH:24][CH2:25][CH:26]([OH:29])[CH2:27]Cl)=[CH:10][CH:9]=1>CO>[O:29]1[CH2:27][CH:26]1[CH2:25][NH:24][C:11]1[C:12]2[C:13](=[O:23])[C:14]3[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:20](=[O:22])[C:21]=2[C:8]([NH:7][CH2:6][CH:5]2[O:30][CH2:4]2)=[CH:9][CH:10]=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-dione

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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.

Workup

  1. customat 60° C
  2. customthe solvent was removed under reduced pressure
  3. customThe residual solid was then purified by flash column chromatography (silica gel, CH2Cl2 : MeOH/25:1)
  4. customRecrystallization from CH2Cl2

Sources & evidence

ORD record
ord-ce5cbadd629846b284dc032d6f5dc954
Source dataset
uspto-grants-1994_09
Patent number
US05344841

Reaction notes

Loading…