Hydrochloric Acid → 9,10-Anthracenedione, 1,4-bis((2-(diethylamino)ethyl)amino)-

HRID 654536Notes

Reaction equation

HRID 654536 reaction equation
O[C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:17])[C:6]=2[C:5](O)=[CH:4][CH:3]=1.S(S([O-])=O)([O-])=O.[Na+].[Na+].[CH2:27]([N:29]([CH2:33][CH3:34])[CH2:30][CH2:31][NH2:32])[CH3:28].Cl>O.C(O)C>[CH2:27]([N:29]([CH2:33][CH3:34])[CH2:30][CH2:31][NH:32][C:5]1[C:6]2[C:7](=[O:17])[C:8]3[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:14](=[O:16])[C:15]=2[C:2]([NH:32][CH2:31][CH2:30][N:29]([CH2:33][CH3:34])[CH2:27][CH3:28])=[CH:3][CH:4]=1)[CH3:28]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6688QuinizarinHCID 24489Sodium DithioniteHCID 60993N,N-Diethylethylenediamine

Product 1

HCID 1531669,10-Anthracenedione, 1,4-bis((2-(diethylamino)ethyl)amino)-Yield 7.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 5 g (0.021 mol) of 1,4-dihydroxyanthracene-9,10-dione and 2 g (0.014 mol) of sodium dithionite in 20 ml water is stirred whilst heating under nitrogen at 90° C. until the mixture turns from orange to brown indicating the presence of 2,3-dihydro(leuco)-1,4-dihydroxyanthracene-9,10-dione. To this reaction mixture is added dropwise 20 g (0.17 mol) of 2-(diethylamino)-ethylamine over a 30 minute period. The mixture is heated at 50°-55° C. for 2 hours and 20 ml of ethanol are added. The solution is then aerated and 200 ml of 2M hydrochloric acid are added. The acidic mixture is washed with 3×200 ml of diethylether followed by 3×200 ml of chloroform. The aqueous phase is made alkaline by the addition of sodium hydroxide solution and extracted with 3×200 ml chloroform. The mixture is evaporated in vacuo to a 5 ml volume and subjected to flash chromatography using a column of 70-230 mesh (60 A) silica gel (SiO2) and an eluting solvent of chloroform followed by chloroform:methanol (1:1 v/v). The blue black material removed from the column in chloroform/methanol is evaporated in vacuo to yield 0.7 g of the title compound, m.p. 107.5°-108.5° C.; λmax λmax (deionised water) (E/cm/M) 256 nm (50950), 584 nm (18650).

Workup

  1. temperatureThe mixture is heated at 50°-55° C. for 2 hours
  2. washThe acidic mixture is washed with 3×200 ml of diethylether
  3. additionby the addition of sodium hydroxide solution
  4. extractionextracted with 3×200 ml chloroform
  5. customThe mixture is evaporated in vacuo to a 5 ml volume
  6. customThe blue black material removed from the column in chloroform/methanol
  7. customis evaporated in vacuo

Sources & evidence

ORD record
ord-cc8dfbdf87df4f74bc217ec18592ca4c
Source dataset
uspto-grants-1992_07
Patent number
US05132327

Reaction notes

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