Reaction #1106666

Reaction equation

1,5-dichloroanthraquinone

N,N,N′-trimethylethylenediamine

→

Compound 9

1,5-bis((2-(dimethylamino)ethyl)(methyl)amino)anthracene-9,10-dione

Solvents

water

Conditions

Workup

1. 1
   Temperaturewas refluxed for 18 h
2. 2
   Extractionextracted with chloroform (2×200 mL)
3. 3
   WashThe combined organic layer was washed with water, brine
4. 4
   Dryingdried over MgSO4
5. 5
   Otherevaporated to dryness
6. 6
   OtherThe residue thus obtained
7. 7
   Otherwas purified by silica gel flash chromatography [CHCl3/MeOH/Et3N (44:5:1)]

Procedure

A mixture of 1,5-dichloroanthraquinone (5.5 g, 20 mmol) and N,N,N′-trimethylethylenediamine (40 ml) was refluxed for 18 h. The mixture was cooled to room temperature, diluted with water (400 mL) and extracted with chloroform (2×200 mL). The combined organic layer was washed with water, brine, dried over MgSO4 and evaporated to dryness. The residue thus obtained was purified by silica gel flash chromatography [CHCl3/MeOH/Et3N (44:5:1)] to provide Compound 9. Abs (max, PBS pH 7.4)=508 nm. The structure of Compound 9 is given below:

Source