Mitoxantrone → HCID 13233893, compound

HRID 647784Notes

Reaction equation

HRID 647784 reaction equation
[OH:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[C:9]([NH:24][CH2:25][CH2:26][NH:27][CH2:28][CH2:29][OH:30])[CH:10]=[CH:11][C:12]=3[NH:17][CH2:18][CH2:19][NH:20][CH2:21][CH2:22][OH:23])[C:7](=[O:31])[C:6]=2[C:5]([OH:32])=[CH:4][CH:3]=1.[O:33]1[CH:37]=[CH:36][CH:35]=[C:34]1[CH:38]=O>C1C=CC=CC=1>[O:33]1[CH:37]=[CH:36][CH:35]=[C:34]1[CH:38]1[N:27]([CH2:26][CH2:25][NH:24][C:9]2[C:8]3[C:7](=[O:31])[C:6]4[C:15](=[C:2]([OH:1])[CH:3]=[CH:4][C:5]=4[OH:32])[C:14](=[O:16])[C:13]=3[C:12]([NH:17][CH2:18][CH2:19][N:20]3[CH2:3][CH2:2][O:1][CH:21]3[C:22]3[O:23][CH:4]=[CH:5][CH:6]=3)=[CH:11][CH:10]=2)[CH2:28][CH2:29][O:30]1

Participants

4

Reactant 2

HCID 4212MitoxantroneHCID 7362Furfural

Product 1

HCID 13233893HCID 13233893, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A suspension of 3.11 g. of 1,4-dihydroxy-5,8-bis[[2-(2-hydroxyethylamino)ethyl]amino]anthraquinone [prepared as described in Example 1(A)] in 55.0 ml. of benzene containing 2.02 g. of 2-furaldehyde is stirred and heated under reflux using a Dean-Stark trap. A total of 0.2 ml. of water is collected as distillate over a 3 hour period, with no additional water after a total of 7 hours of refluxing. The hot solution is filtered, removing a small amount of blue-black solid. The filtrate is concentrated and petroleum ether is added to give a gum which slowly solidifies. The solid is collected and washed with benzene to give 2.05 g. of a blue-black solid.

Workup

  1. additionA suspension of 3.11 g
  2. temperatureheated
  3. temperatureunder reflux
  4. distillationof water is collected as distillate over a 3 hour period, with no additional water after a total of 7 hours
  5. temperatureof refluxing
  6. filtrationThe hot solution is filtered
  7. customremoving a small amount of blue-black solid
  8. concentrationThe filtrate is concentrated
  9. additionpetroleum ether is added
  10. customto give a gum which
  11. customThe solid is collected
  12. washwashed with benzene
  13. customto give 2.05 g

Sources & evidence

ORD record
ord-15ba159705594ff5a6cf3c38ebe441c2
Source dataset
uspto-grants-1983_10
Patent number
US04410524

Reaction notes

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