Mitoxantrone → HCID 13233915, compound

HRID 647786Notes

Reaction equation

HRID 647786 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.[CH3:33][N:34]([CH3:43])[C:35]1[CH:42]=[CH:41][C:38]([CH:39]=O)=[CH:37][CH:36]=1>C1(C)C=CC=CC=1>[CH3:33][N:34]([CH3:43])[C:35]1[CH:42]=[CH:41][C:38]([CH:39]2[N:27]([CH2:26][CH2:25][NH:24][C:9]3[C:8]4[C:7](=[O:31])[C:6]5[C:15](=[C:2]([OH:1])[CH:3]=[CH:4][C:5]=5[OH:32])[C:14](=[O:16])[C:13]=4[C:12]([NH:17][CH2:18][CH2:19][N:20]4[CH2:21][CH2:22][O:23][CH:39]4[C:38]4[CH:41]=[CH:42][C:35]([N:34]([CH3:43])[CH3:33])=[CH:36][CH:37]=4)=[CH:11][CH:10]=3)[CH2:28][CH2:29][O:30]2)=[CH:37][CH:36]=1

Participants

4

Reactant 2

HCID 4212MitoxantroneHCID 74794-(Dimethylamino)Benzaldehyde

Product 1

HCID 13233915HCID 13233915, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

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 60 ml. of toluene containing 3.13 g. of p-dimethylaminobenzaldehyde is stirred and heated at reflux for 5 hours by the procedure of Example 1(B). The hot reaction solution is filtered and is allowed to stand for several days. The crystallized product is collected by filtration and washed with toluene to yield 4.34 g. of the product of the Example as dark-blue crystals, m.p. 150°-154° C.

Workup

  1. additionA suspension of 3.11 g
  2. temperatureheated
  3. temperatureat reflux for 5 hours by the procedure of Example 1(B)
  4. filtrationThe hot reaction solution is filtered
  5. waitto stand for several days
  6. filtrationThe crystallized product is collected by filtration
  7. washwashed with toluene
  8. customto yield 4.34 g

Sources & evidence

ORD record
ord-ed4fffc23db44382b17f8f0659f96422
Source dataset
uspto-grants-1983_10
Patent number
US04410524

Reaction notes

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