反応 #1174124

ord-fdc13a55f8cd4913a73de2829c115f78

反応方程式

O=C1c2cccc(Cl)c2C(=O)c2c(Cl)cccc21
1,8-dichloroanthraquinone
CC(C)(CN)CO
3-amino-2,2-dimethylpropanol
Cl
hydrochloric acid
CC(C)(CO)CNc1cccc2c1C(=O)c1c(NCC(C)(C)CO)cccc1C2=O
1,8 -bis[(3-hydroxy-2,2-dimethylpropyl)amino]anthraquinone

反応条件

温度
130°CELSIUS
詳細条件
See reaction.notes.procedure_details.

実験手順

A mixture of 1,8-dichloroanthraquinone (13.8 g, 0.05 mol), 3-amino-2,2-dimethylpropanol (20.6 g, 0.20 mol) and 2-ethoxyethanol (100 mL) is heated at about 130° C. for 20 hours. The reaction mixture is drowned into water (1L) and the mixture is acidified with concentrated hydrochloric acid. The product, 1,8 -bis[(3-hydroxy-2,2-dimethylpropyl)amino]anthraquinone, is obtained in an essentially quantitative yield by filtering, washing with water and drying in air. Recrystallization from toluene, followed by filtration, washing with hexane and air drying gives 16.0 g of purified crystalline product. The product may be purified further by recrystallization from methanol. Thin layer chromatography shows that the product contains only one colored component and mass spectrometry analysis is consistent with 1,8-bis[(3-hydroxy-2,2-dimethylpropyl)amino]anthraquinone. The bluish-red product has an absorption maximum at 556 nm and an extinction coefficient (ε) of 12,228 in methylene chloride.

出典

DOI: 10.6084/m9.figshare.5104873.v1特許: US05032670uspto-grants-1991_07