Quinizarin → 9,10-Anthracenedione, 1,4-bis((2-(diethylamino)ethyl)amino)-

HRID 1719471Notes

Reaction equation

HRID 1719471 reaction equation
[CH2:1]([N:3]([CH2:7][CH3:8])[CH2:4][CH2:5][NH2:6])[CH3:2].[CH:9]1[CH:10]=[CH:11][C:12]2[C:23](=[O:24])[C:22]3[C:17](=[C:18](O)[CH:19]=[CH:20][C:21]=3O)[C:15](=[O:16])[C:13]=2[CH:14]=1>>[CH2:1]([N:3]([CH2:7][CH3:8])[CH2:4][CH2:5][NH:6][C:18]1[C:17]2[C:15](=[O:16])[C:13]3[C:12](=[CH:11][CH:10]=[CH:9][CH:14]=3)[C:23](=[O:24])[C:22]=2[C:21]([NH:6][CH2:5][CH2:4][N:3]([CH2:7][CH3:8])[CH2:1][CH3:2])=[CH:20][CH:19]=1)[CH3:2]

Participants

3

Reactant 2

HCID 6688QuinizarinHCID 60993N,N-Diethylethylenediamine

Product 1

HCID 1531669,10-Anthracenedione, 1,4-bis((2-(diethylamino)ethyl)amino)-

Procedure

A mixture of 42 ml. of N,N,N',N'-tetramethylenediamine, 17.43 g. of N,N-diethylethylenediamine and 12.01 g. of quinizarin is stirred and heated under reflux for 15 hours. The resulting solution is evaporated to dryness and a chloroform solution of the residue is filtered through 300 g. of alumina. The blue filtrate is chromatographed on silica gel in a Nylon® film column, developing with a chloroform:methanol (6:1) mixture. The major blue band is cut out and then eluted with a chloroform:methanol:triethylamine (6:2:1) mixture. The eluate is evaporated. The residue is crystallized from hexane and washed with petroleum ether, giving 1.43 g. of the desired product as blue-black plates, mp. 109° C.

Workup

  1. additionA mixture of 42 ml
  2. temperatureheated
  3. temperatureunder reflux for 15 hours
  4. customThe resulting solution is evaporated to dryness
  5. filtrationa chloroform solution of the residue is filtered through 300 g
  6. customThe blue filtrate is chromatographed on silica gel in a Nylon® film column
  7. washeluted with a chloroform:methanol:triethylamine (6:2:1) mixture
  8. customThe eluate is evaporated
  9. customThe residue is crystallized from hexane
  10. washwashed with petroleum ether
  11. customgiving 1.43 g

Sources & evidence

ORD record
ord-60a412220a2d439d95fb905fc231100b
Source dataset
uspto-grants-1985_09
Patent number
US04540583

Reaction notes

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