Reaction #1106667

Reaction equation

1,5-dichloro anthraquinone

N,N-dimethylethylenediamine

→

Compound 17

Yield 16.9%

1-Chloro-5-(2-(dimethylamino)ethylamino)anthracene-9,10-dione

Yield 16.9%

Solvents

N,N-dimethylacetamide

Conditions

Workup

1. 1
   Temperatureheated in an oil bath (T=100° C.) for 45 minutes
2. 2
   OtherReaction mixture
3. 3
   Temperaturewas cooled
4. 4
   Filtrationfiltered
5. 5
   workup.ADDITIONTo the filtrate petroleum ether (50 mL) was added
6. 6
   workup.STIRRINGwas stirred at 4° C. over night
7. 7
   OtherPrecipitated solid
8. 8
   Otherwas removed by filtration and supernatant
9. 9
   Otherwas evaporated to dryness, co-evaporated with chloroform
10. 10
    Otherdried under vacuum
11. 11
    OtherThe crude dye was then purified on Biotage SP4 system
12. 12
    Otherevaporated to dryness

Procedure

A mixture of 1,5-dichloro anthraquinone (5.0 g, 18.0 mmol), N,N-dimethylacetamide (30 mL) and N,N-dimethylethylenediamine (2 mL, 18 mmol) was stirred at room temperature for 1 hour and then heated in an oil bath (T=100° C.) for 45 minutes. Reaction mixture was cooled and filtered. To the filtrate petroleum ether (50 mL) was added and combined mixture was stirred at 4° C. over night. Precipitated solid was removed by filtration and supernatant was evaporated to dryness, co-evaporated with chloroform and dried under vacuum. The crude dye was then purified on Biotage SP4 system using a gradient of methanol in chloroform. Appropriate fractions were combined and evaporated to dryness to provide Compound 17 (1.0 g) as a red solid. Rf (9:1 CHCl3/MeOH): 0.46; Abs (max, PBS)=500 nm. The structure of Compound 17 is given below:

Source