Reacción #1106668

ord-1a12c87f41054061aa0a5b8452b10717

Ecuación de reacción

CN(C)CCNc1cccc2c1C(=O)c1cccc(Cl)c1C2=O
Compound 17
CN(C)CCNc1cccc2c1C(=O)c1cccc(Cl)c1C2=O
1-Chloro-5-(2-(dimethylamino)ethylamino)anthracene-9,10-dione
NCCO
ethanolamine
CN(C)CCNc1cccc2c1C(=O)c1cccc(NCCO)c1C2=O
Compound 21
Rendimiento 38.8%
CN(C)CCNc1cccc2c1C(=O)c1cccc(NCCO)c1C2=O
1-(2-(dimethylamino)ethylamino)-5-(2-hydroxyl ethylamino)anthracene-9,10-dione
Rendimiento 38.8%

Disolventes

Condiciones de reacción

Temperatura
-150°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    TemperaturaThe mixture was cooled to room temperature
  2. 2
    Extracciónextracted with water and brine
  3. 3
    SecadoThe organic layer was dried (Na2SO4)
  4. 4
    Otroevaporated

Procedimiento

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:

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08715944B2uspto-grants-2014_05