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

HRID 1019483Notes

Reaction equation

HRID 1019483 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-98b4b17fa882481e9b2d696cfe3eed5d
Source dataset
uspto-grants-2014_05
Patent number
US08715944B2

Reaction notes

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