1,8-Dichloroanthraquinone → 1,8-Bis{[2-(dimethylamino)ethyl]amino}anthracene-9,10-dione

HRID 522935

Reaction equation

HRID 522935 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.[CH3:19][N:20]([CH3:24])[CH2:21][CH2:22][NH2:23]>O>[CH3:19][N:20]([CH3:24])[CH2:21][CH2:22][NH:23][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:23][CH2:22][CH2:21][N:20]([CH3:24])[CH3:19])[C:7](=[O:18])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 67081,8-DichloroanthraquinoneHCID 66053N,N-Dimethylethylenediamine

Product 1

HCID 143201191,8-Bis{[2-(dimethylamino)ethyl]amino}anthracene-9,10-dione

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1,8-dichloroanthraquinone (5.5 g, 20 mmol) and N,N-dimethylethylenediamine (40 mL) was refluxed for 18 h. The mixture was cooled to room temperature and diluted with water to precipitate the title compound which was recrystallised from methanol to afford Compound 6 (4.5 g). The structure of Compound 6 is given below:

Workup

  1. temperaturewas refluxed for 18 h
  2. customto precipitate the title compound which
  3. customwas recrystallised from methanol

Sources & evidence

ORD record
ord-0272c4eb373b4ee89275b9904cf25ac8
Source dataset
uspto-grants-2016_05
Patent number
US09334281B2

Linked notes

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