1,4,5,8-Tetrahydroxy-9,10-anthracenedione → 9,10-Anthracenedione, 1,4,5-trihydroxy-8-((2-((2-hydroxyethyl)amino)ethyl)amino)-

HRID 1680617

Reaktionsgleichung

Reaktionsgleichung von HRID 1680617
O[C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[C:9]([OH:18])[CH:10]=[CH:11][C:12]=3[OH:17])[C:7](=[O:19])[C:6]=2[C:5]([OH:20])=[CH:4][CH:3]=1.[NH2:21][CH2:22][CH2:23][NH:24][CH2:25][CH2:26][OH:27].CN(C)CCN(C)C>>[OH:27][CH2:26][CH2:25][NH:24][CH2:23][CH2:22][NH:21][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[C:9]([OH:18])[CH:10]=[CH:11][C:12]=3[OH:17])[C:7](=[O:19])[C:6]=2[C:5]([OH:20])=[CH:4][CH:3]=1

Komponenten

4

Edukt 3

HCID 66861,4,5,8-Tetrahydroxy-9,10-anthracenedioneHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 8112N-(2-Hydroxyethyl)ethylenediamine

Produkt 1

HCID 1495859,10-Anthracenedione, 1,4,5-trihydroxy-8-((2-((2-hydroxyethyl)amino)ethyl)amino)-

Versuchsvorschrift

A suspension of 5.44 g. of 1,4,5,8-tetrahydroxy-9,10-anthracenedione [P. G. Marshall, J.C.S., 254 (1937)] in a solution of 2.08 g. of 2-(2-aminoethylamino)ethanol in 50 ml. of N,N,N',N'-tetramethylethylenediamine is stirred and heated under reflux for 17 hours, then allowed to cool. The solid is collected by filtration and washed 3 times with N,N,N',N'-tetramethylethylenediamine, then twice with hexane. The first filtrate and the diamine washings are combined and the solution is allowed to stand for 60 hours as a solid separates. This solid is collected and washed as above to give 0.524 g. of a dark blue solid. This solid is purified by dry column chromatography on deactivated (i.e., air-equilibrated) silica gel by the procedure of B. Loev and M. M. Goodman [Chem. and Ind., 2026 (1967)], eluting with chloroform-methanol (3:1) and monitoring the eluate fractions by thin layer chromatography on silica gel with the same solvent mixture. The cuts which showed only the slower of two purple spots were pooled and evaporated to give 0.42 g. of the product of the Example as a dark blue solid, mp. 196°-198° C.

Aufarbeitung

  1. additionA suspension of 5.44 g
  2. temperatureheated
  3. temperatureunder reflux for 17 hours
  4. temperatureto cool
  5. filtrationThe solid is collected by filtration
  6. washwashed 3 times with N,N,N',N'-tetramethylethylenediamine
  7. customThis solid is collected
  8. washwashed as above
  9. customto give 0.524 g
  10. customThis solid is purified
  11. customby dry column chromatography on deactivated (i.e., air-equilibrated) silica gel by the procedure of B
  12. washGoodman [Chem. and Ind., 2026 (1967)], eluting with chloroform-methanol (3:1)
  13. customevaporated
  14. customto give 0.42 g

Quellen und Nachweise

ORD-Eintrag
ord-2cbdee36df1947019e08e28a410a2952
Quelldatensatz
uspto-grants-1981_06
Patentnummer
US04275009

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