Hydrochloric Acid → HCID 19818793, compound

HRID 1086942Notes

Reaction equation

HRID 1086942 reaction equation
Cl[C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][C:12]=3Cl)[C:7](=[O:18])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[NH2:19][CH2:20][C:21]([CH3:25])([CH3:24])[CH2:22][OH:23].Cl>C(OCCO)C>[OH:23][CH2:22][C:21]([CH3:25])([CH3:24])[CH2:20][NH:19][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][C:12]=3[NH:19][CH2:20][C:21]([CH3:25])([CH3:24])[CH2:22][OH:23])[C:7](=[O:18])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 67081,8-DichloroanthraquinoneHCID 1173261-Propanol, 3-amino-2,2-dimethyl-

Product 1

HCID 19818793HCID 19818793, compound

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent2×

Conditions

Temperature
130 °C

Procedure

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.

Sources & evidence

ORD record
ord-fdc13a55f8cd4913a73de2829c115f78
Source dataset
uspto-grants-1991_07
Patent number
US05032670

Reaction notes

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