1,5-Dichloroanthraquinone → 1,5-Bis((2-(dimethylamino)ethyl)(methyl)amino)anthracene-9,10-dione

HRID 522936Notes

Reaction equation

HRID 522936 reaction equation
Cl[C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[C:9](Cl)[CH:10]=[CH:11][CH:12]=3)[C:7](=[O:18])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH3:19][N:20]([CH3:25])[CH2:21][CH2:22][NH:23][CH3:24]>O>[CH3:19][N:20]([CH3:25])[CH2:21][CH2:22][N:23]([CH3:24])[C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[C:9]([N:23]([CH2:22][CH2:21][N:20]([CH3:25])[CH3:19])[CH3:24])[CH:10]=[CH:11][CH:12]=3)[C:7](=[O:18])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 67111,5-DichloroanthraquinoneHCID 673381,2-Ethanediamine, N1,N1,N2-trimethyl-

Product 1

HCID 592291181,5-Bis((2-(dimethylamino)ethyl)(methyl)amino)anthracene-9,10-dione

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1,5-dichloroanthraquinone (5.5 g, 20 mmol) and N,N,N′-trimethylethylenediamine (40 ml) was refluxed for 18 h. The mixture was cooled to room temperature, diluted with water (400 mL) and extracted with chloroform (2×200 mL). The combined organic layer was washed with water, brine, dried over MgSO4 and evaporated to dryness. The residue thus obtained was purified by silica gel flash chromatography [CHCl3/MeOH/Et3N (44:5:1)] to provide Compound 9. Abs (max, PBS pH 7.4)=508 nm. The structure of Compound 9 is given below:

Workup

  1. temperaturewas refluxed for 18 h
  2. extractionextracted with chloroform (2×200 mL)
  3. washThe combined organic layer was washed with water, brine
  4. dry with materialdried over MgSO4
  5. customevaporated to dryness
  6. customThe residue thus obtained
  7. customwas purified by silica gel flash chromatography [CHCl3/MeOH/Et3N (44:5:1)]

Sources & evidence

ORD record
ord-e3151e542a2f4975a8558c2400efa07e
Source dataset
uspto-grants-2016_05
Patent number
US09334281B2

Reaction notes

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