Acryloyl chloride → (4-Heptylphenyl)-4-acrylamido-1-aminoanthraquinone-2-carboxylate

HRID 28314Notes

Reaction equation

C(OCCCCCCOC1C=CC([C:19]2[C:20]([C:37]([O-:39])=[O:38])=[C:21]([NH2:36])[C:22]3[C:23](=[O:35])[C:24]4[C:29]([C:30](=[O:34])[C:31]=3[C:32]=2[NH2:33])=[CH:28][CH:27]=[CH:26][CH:25]=4)=CC=1)(=O)C=C.[C:40](Cl)(=[O:43])[CH:41]=[CH2:42]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH2:23]([C:22]1[CH:21]=[CH:20][C:19]([O:39][C:37]([C:20]2[CH:19]=[C:32]([NH:33][C:40](=[O:43])[CH:41]=[CH2:42])[C:31]3[C:30](=[O:34])[C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[C:23](=[O:35])[C:22]=3[C:21]=2[NH2:36])=[O:38])=[CH:32][CH:31]=1)[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]

Participants

Conditions

Temperature: 0 °C

Procedure

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.

Workup

stirringstirring
waitwas continued for further 60 min
concentrationThe reaction mixture was then concentrated to half its volume
customThe afforded violet solid was further recrystallised from ethanol/methylenechloride 9/1 (v/v)

Sources & evidence

ORD record: ord-137a47f60bb046b181368db7f0542f86
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07419620B2

Reaction notes

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