Ethanolamine → 1-(2-(Dimethylamino)ethylamino)-5-(2-hydroxyl ethylamino)anthracene-9,10-dione

HRID 1019486Notes

Reaction equation

Cl[C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[C:9]([NH:17][CH2:18][CH2:19][N:20]([CH3:22])[CH3:21])[CH:10]=[CH:11][CH:12]=3)[C:7](=[O:23])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH2:24]([CH2:26][NH2:27])[OH:25]>C(Cl)Cl>[CH3:21][N:20]([CH3:22])[CH2:19][CH2:18][NH:17][C:9]1[C:8]2[C:7](=[O:23])[C:6]3[C:15](=[C:2]([NH:27][CH2:26][CH2:24][OH:25])[CH:3]=[CH:4][CH:5]=3)[C:14](=[O:16])[C:13]=2[CH:12]=[CH:11][CH:10]=1

Participants

Conditions

Temperature: -150 °C

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:

Workup

temperatureThe mixture was cooled to room temperature
extractionextracted with water and brine
dry with materialThe organic layer was dried (Na2SO4)
customevaporated

Sources & evidence

ORD record: ord-1a12c87f41054061aa0a5b8452b10717
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08715944B2

Reaction notes

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