Reacción #56592

Ecuación de reacción

(4-heptylphenyl)-1,4-diaminoanthraquinone-2-carboxylate

4-(6-Acryloyloxyhexyloxy)phenyl-1,4diaminoanthraquinone-2-carboxylate

acryloylchloride

→

(4-heptylphenyl)-4-acrylamido-1-aminoanthraquinone-2-carboxylate

Rendimiento 199.8%

Disolventes

methylenechloride

methylenechloride

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGstirring
2. 2
   workup.WAITwas continued for further 60 min
3. 3
   ConcentraciónThe reaction mixture was then concentrated to half its volume
4. 4
   OtroThe afforded violet solid was further recrystallised from ethanol/methylenechloride 9/1 (v/v)

Procedimiento

To a stirred solution of 0.91 g of (4-heptylphenyl)-1,4-diaminoanthraquinone-2-carboxylate (preparation analogous to example 1) in 80 ml of methylenechloride, cooled to 0° C. was added dropwise (over a period of 30 min) a solution of 0.36 g of acryloylchloride in 20 ml of methylenechloride. After stirring for 1 h at 0° C. and 30 min at room temperature, DMAP was added and stirring was continued for further 60 min. The reaction mixture was then concentrated to half its volume and passed through a silica gel column using methylenechloride as the eluent. The afforded violet solid was further recrystallised from ethanol/methylenechloride 9/1 (v/v) to give 0.88 g (4-heptylphenyl)-4-acrylamido-1-aminoanthraquinone-2-carboxylate as violet crystals; λmax. (CB 483): 572 nm.

Fuente