1,3-Propanediamine → Anthraquinone, 1,4-bis(3-(aminopropyl)amino)-5,8-dihydroxy-

HRID 1649538Notes

Reaction equation

HRID 1649538 reaction equation
[CH2:1]1[C:15](=[O:16])[C:14]2[C:5](=[C:6]([OH:20])[C:7]3[C:12]([C:13]=2[OH:17])=[C:11](O)[CH:10]=[CH:9][C:8]=3O)[C:3](=[O:4])[CH2:2]1.[NH2:21][CH2:22][CH2:23][CH2:24][NH2:25]>>[NH2:21][CH2:22][CH2:23][CH2:24][NH:25][C:8]1[C:7]2[C:6](=[O:20])[C:5]3[C:14](=[C:15]([OH:16])[CH:1]=[CH:2][C:3]=3[OH:4])[C:13](=[O:17])[C:12]=2[C:11]([NH:21][CH2:22][CH2:23][CH2:24][NH2:25])=[CH:10][CH:9]=1

Participants

3

Reactant 2

HCID 4281,3-PropanediamineHCID 664859,10-Anthracenedione, 2,3-dihydro-1,4,5,8-tetrahydroxy-

Product 1

HCID 167850Anthraquinone, 1,4-bis(3-(aminopropyl)amino)-5,8-dihydroxy-

Conditions

Temperature
45 °C

Procedure

A suspension of 10.0 g. of leuco-1,4,5,8-tetrahydroxyanthraquinone in 120 ml. of de-aerated 1,3-diaminopropane is stirred and heated at 45° C. under nitrogen for one hour and then for 10 minutes as air is bubbled into the suspension. The mixture is then evaporated to dryness and the residue is extracted with 650 ml. of ethanol in a Soxhlet apparatus for 17 hours. The extract is filtered while hot, concentrated to 95 ml. and then diluted with 900 ml. of diethyl ether. The mixture is cooled and the solid is collected, washed with ethanol-diethyl ether, then diethyl ether giving the desired product as 9.57 g. of a blue solid, mp. 115°-130° C.

Workup

  1. additionA suspension of 10.0 g
  2. customfor 10 minutes as air is bubbled into the suspension
  3. customThe mixture is then evaporated to dryness
  4. extractionthe residue is extracted with 650 ml
  5. filtrationThe extract is filtered while hot,
  6. concentrationconcentrated to 95 ml
  7. additionand then diluted with 900 ml
  8. temperatureThe mixture is cooled
  9. customthe solid is collected
  10. washwashed with ethanol-diethyl ether

Sources & evidence

ORD record
ord-11405828e19f4a44979e99737edccbf3
Source dataset
uspto-grants-1983_11
Patent number
US04418078

Reaction notes

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