1,5-Dichloroanthraquinone → HCID 13558462, compound

HRID 637586Notes

Reaction equation

HRID 637586 reaction equation
Cl[C:2]1[C:15]2[C:14](=O)[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.[NH:19]([CH2:21][CH2:22][NH:23][CH2:24][CH2:25][OH:26])[NH2:20].[C:27](=[O:30])(O)[O-].[K+].[F-].[K+]>CS(C)=O>[OH:26][CH2:25][CH2:24][NH:23][CH2:22][CH2:21][N:19]1[C:2]2[CH:3]=[CH:4][CH:5]=[C:6]3[C:7](=[O:18])[C:8]4[C:13]([C:14]([C:15]=23)=[N:20]1)=[CH:12][CH:11]=[CH:10][C:9]=4[NH:19][CH2:21][CH2:22][NH:23][CH2:24][CH2:27][OH:30]

Participants

6

Reactant 4

HCID 67111,5-DichloroanthraquinoneHCID 516893Potassium BicarbonateHCID 522689Potassium FluorideHCID 134138082-[(2-Hydrazinylethyl)amino]ethan-1-ol

Product 1

HCID 13558462HCID 13558462, compoundYield 15.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 11.1 g (40 mmol) of 1,5-dichloro-9,10-anthracenedione, 13.1 g (110 mmol) of 2-[(hydrazinoethyl)amino]ethanol, 4 g of anhydrous potassium bicarbonate, 1 g of anhydrous potassium fluoride, and 110 ml of dimethyl sulfoxide is stirred at 70° C. overnight. The mixture is chilled and the solids are collected by filtration, washed with water, then thoroughly with acetonitrile to give a residue that is crystallized from 2-propanol to leave 2.6 g of product. The hydrochloride salt is prepared as described in Example 3; mp 272°-273° C. (decomposition).

Workup

  1. temperatureThe mixture is chilled
  2. filtrationthe solids are collected by filtration
  3. washwashed with water
  4. customthoroughly with acetonitrile to give a residue that
  5. customis crystallized from 2-propanol

Sources & evidence

ORD record
ord-6f7a9a3bc05d4bf2a4544b0aa98aef78
Source dataset
uspto-grants-1985_12
Patent number
US04556654

Reaction notes

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