Reaction #1106668

Reaction equation

Compound 17

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

ethanolamine

→

Compound 21

Yield 38.8%

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

Yield 38.8%

Solvents

CH2Cl2

Conditions

Workup

1. 1
   TemperatureThe mixture was cooled to room temperature
2. 2
   Extractionextracted with water and brine
3. 3
   DryingThe organic layer was dried (Na2SO4)
4. 4
   Otherevaporated

Procedure

A mixture of Compound 17 (0.87 g, 2.7 mmol) and ethanolamine (0.8 mL, 13.23 mmol) was heated in an oil bath (−150° C.) for 18 hours. The mixture was cooled to room temperature, dissolved in 100 mL CH2Cl2 and extracted with water and brine. The organic layer was dried (Na2SO4) and evaporated to provide Compound 21 (370 mg). This product was used in the next step without any purification. Rf (9:1 CHCl3/MeOH) 0.19. The structure of Compound 21 is given below:

Source