Water → 9,10-Anthracenedione, 1,4-bis((3-chloro-2-hydroxypropyl)amino)-

HRID 1110435Notes

Reaction equation

HRID 1110435 reaction equation
[NH2:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:17])[C:6]=2[C:5]([NH2:18])=[CH:4][CH:3]=1.[OH2:19].[CH2:20]([CH:22]1[O:24][CH2:23]1)[Cl:21]>C(O)(=O)C>[Cl:21][CH2:20][CH:22]([OH:19])[CH2:23][NH:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:17])[C:6]=2[C:5]([NH:18][CH2:23][CH:22]([OH:24])[CH2:20][Cl:21])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 7835Epichlorohydrin3×HCID 31420Disperse Violet 1

Product 1

HCID 1218099,10-Anthracenedione, 1,4-bis((3-chloro-2-hydroxypropyl)amino)-

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
50 °C

Procedure

1,4-Diaminoanthraquinone (20.00 g, 0.084 mole) was slurried in 200 ml of glacial acetic acid containing 12 ml of water. This mixture was heated to 50° C. and treated with 8.0 ml of epichlorohydrin. The reaction temperature was raised to between 90° and 100° C. and the remaining 32 ml of epichlorohydrin was dripped in slowly during 3.5 hours while maintaining this temperature range. A total of 40 ml (0.511 mole) of epichlorohydrin was added to the reaction mixture. After addition was complete, the external heating source was removed and the reaction mixture was allowed to cool to ambient temperature and stir overnight (about 16 hours). 200 ml of acetic acid containing 20% water was added to the reaction mixture and stirring was continued for 2 hours. The precipitated product was isolated by filtration. The filter-cake was rinsed with 20% aqueous acetic acid, followed by distilled water and then air-dried. This material was further dried in-vacuo over P2O5 to afford 19.08 g of 1,4-bis-(3-chloro-2-hydroxypropylamino)-9,10-anthracenedione.

Workup

  1. temperatureThe reaction temperature was raised to between 90° and 100° C.
  2. customslowly during 3.5 hours
  3. temperaturewhile maintaining this temperature range
  4. additionAfter addition
  5. customthe external heating source was removed
  6. temperatureto cool to ambient temperature
  7. addition200 ml of acetic acid containing 20% water was added to the reaction mixture
  8. stirringstirring
  9. waitwas continued for 2 hours
  10. customThe precipitated product was isolated by filtration
  11. washThe filter-cake was rinsed with 20% aqueous acetic acid
  12. distillationby distilled water
  13. customair-dried
  14. dry with materialThis material was further dried in-vacuo over P2O5

Sources & evidence

ORD record
ord-92aaa85e32784eefb93f00c01664ddc3
Source dataset
uspto-grants-1990_12
Patent number
US04975459

Reaction notes

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