1,5-Dichloroanthraquinone → 9,10-Anthracenedione, 1,5-bis((2-(diethylamino)ethyl)amino)-

HRID 654535Notes

Reaction equation

HRID 654535 reaction equation
Cl[C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[C:9](Cl)[CH:10]=[CH:11][CH:12]=3)[C:7](=[O:18])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH2:19]([N:21]([CH2:25][CH3:26])[CH2:22][CH2:23][NH2:24])[CH3:20]>Cl>[CH2:19]([N:21]([CH2:25][CH3:26])[CH2:22][CH2:23][NH:24][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[C:9]([NH:24][CH2:23][CH2:22][N:21]([CH2:25][CH3:26])[CH2:19][CH3:20])[CH:10]=[CH:11][CH:12]=3)[C:7](=[O:18])[C:6]=2[CH:5]=[CH:4][CH:3]=1)[CH3:20]

Participants

4

Reactant 2

HCID 67111,5-DichloroanthraquinoneHCID 60993N,N-Diethylethylenediamine

Product 1

HCID 1648639,10-Anthracenedione, 1,5-bis((2-(diethylamino)ethyl)amino)-Yield 59.6%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 5.52 g (0.02 mol) of 1,5-dichloroanthracene-9,10-dione in 23.2 g (0.2 mol) of 2-(diethylamino)ethylamine is heated at reflux temperature for 4 hours. The mixture is cooled in an ice-bath and 100 ml concentrated hydrochloric acid is added with stirring. This acidic mixture is extracted with three aliquots of 200 ml of diethylether followed by three aliquots of 200 ml of chloroform. The aqueous layer is collected and made alkaline with sodium hydroxide solution, extracted into chloroform and evaporated in vacuo at 30° C. The oily residue is washed with water, dissolved in methanol and titrated with hydrogen chloride in dry diethyl ether to give a precipitate which is dried to yield 5.2 g of the title compound as the hydrochloride in the form of a dark red solid, m.p. 158.5°-159.5° C.; λmax (deionised water) (E/cm/M) 231 nm (34280), 516 nm (10690).

Workup

  1. temperatureat reflux temperature for 4 hours
  2. temperatureThe mixture is cooled in an ice-bath
  3. extractionThis acidic mixture is extracted with three aliquots of 200 ml of diethylether
  4. customThe aqueous layer is collected
  5. extractionextracted into chloroform
  6. customevaporated in vacuo at 30° C
  7. washThe oily residue is washed with water
  8. dissolutiondissolved in methanol
  9. customto give a precipitate which
  10. customis dried

Sources & evidence

ORD record
ord-c27b243df26145b3b554cfed50266700
Source dataset
uspto-grants-1992_07
Patent number
US05132327

Reaction notes

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