2,6-Dihydroxyanthraquinone → 2-(Diethylamino)ethoxy anthraquinone

HRID 616341

Reaktionsgleichung

Reaktionsgleichung von HRID 616341
O[C:2]1[CH:15]=[CH:14][C:13]2[C:12](=[O:16])[C:11]3[C:6](=[CH:7][CH:8]=[C:9](O)[CH:10]=3)[C:5](=[O:18])[C:4]=2[CH:3]=1.ClC1C=CC=CC=1.Cl.[CH2:27]([N:29]([CH2:33][CH3:34])[CH2:30][CH2:31]Cl)[CH3:28].[OH-:35].[K+]>C(Cl)(Cl)Cl.O>[CH2:27]([N:29]([CH2:33][CH3:34])[CH2:30][CH2:31][O:35][C:10]1[C:11]2[C:12](=[O:16])[C:13]3[C:4](=[CH:3][CH:2]=[CH:15][CH:14]=3)[C:5](=[O:18])[C:6]=2[CH:7]=[CH:8][CH:9]=1)[CH3:28]

Komponenten

7

Edukt 4

HCID 67762,6-DihydroxyanthraquinoneHCID 7964ChlorobenzeneHCID 133631-Chloro-2-(diethylamine)ethane hydrochlorideHCID 14797Potassium Hydroxide

Produkt 1

HCID 4121832-(Diethylamino)ethoxy anthraquinone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

In addition to the methods given in Examples 1 and 2, the following method has also proven useful. To a mixture of 114g (0.6 mole) of 2,6-dihydroxyanthraquinone and 1.2 liters of chlorobenzene was added a solution of 412g (2.4 moles) 2-diethylaminoethyl chloride hydrochloride in 350 ml. of water. With efficient stirring, a solution of 264g (4.0 moles) of potassium hydroxide pellets (85%) in 350 ml. of water was added. The resulting mixture was heated with continued stirring on a steam bath for about 24 hours, then cooled by adding about 500 g of ice. 400 ml. chloroform was added. The lower organic layer was separated and washed several times with water, then dried with anhydrous magnesium sulfate. After filtration, the solvents were removed under reduced pressure in a rotary evaporator. The residue was recrystallized from a mixture of methanol and chloroform as described in Example 1 to give 2,6-bis 2-(diethylamino)ethoxy anthraquinone base, M.P. 178-181° C. The base can be converted to the dihydrochloride salt as described in Example 1.

Aufarbeitung

  1. additionIn addition to the methods
  2. temperatureThe resulting mixture was heated
  3. temperaturecooled
  4. customThe lower organic layer was separated
  5. washwashed several times with water
  6. dry with materialdried with anhydrous magnesium sulfate
  7. filtrationAfter filtration
  8. customthe solvents were removed under reduced pressure in a rotary evaporator
  9. customThe residue was recrystallized from a mixture of methanol and chloroform

Quellen und Nachweise

ORD-Eintrag
ord-258b699b381044cf9af7deada2d9a7dd
Quelldatensatz
uspto-grants-1978_02
Patentnummer
US04073904

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