Ammonia → Mitoxantrone

HRID 986726Notes

Reaction equation

HRID 986726 reaction equation
Cl.Cl.[OH:3][C:4]1[C:17]2[C:16](=[O:18])[C:15]3[C:10](=[C:11]([NH:26][CH2:27][CH2:28][NH:29][CH2:30][CH2:31][OH:32])[CH:12]=[CH:13][C:14]=3[NH:19][CH2:20][CH2:21][NH:22][CH2:23][CH2:24][OH:25])[C:9](=[O:33])[C:8]=2[C:7]([OH:34])=[CH:6][CH:5]=1.N>CO>[OH:34][C:7]1[C:8]2[C:9](=[O:33])[C:10]3[C:15](=[C:14]([NH:19][CH2:20][CH2:21][NH:22][CH2:23][CH2:24][OH:25])[CH:13]=[CH:12][C:11]=3[NH:26][CH2:27][CH2:28][NH:29][CH2:30][CH2:31][OH:32])[C:16](=[O:18])[C:17]=2[C:4]([OH:3])=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 222Ammonia2×HCID 51082Mitoxantrone dihydrochloride

Product 1

HCID 4212MitoxantroneYield 88.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 30.0 g of 1,4-dihydroxy-5,8-bis[[2-(2-hydroxyethylamino)ethyl]amino]anthraquinone dihydrochloride (prepared as described in Example 24 of U.S. Pat. No. 4,197,249) and 300 ml of methanol was chilled in an ice bath in a Dewar flask. The mixture was saturated with ammonia gas and was allowed to stand at 0° C. for one hour with the continuous slow addition of ammonia gas and with periodic stirring. The solid was collected by filtration and washed by slurrying with five 150 ml portions of methanol saturated with ammonia gas to give 22.9 g of 1,4-dihydroxy-5,8-bis[[2-(2-hydroxyethylamino)ethyl]amino]anthraquinone as blue-black micro rods, mp 175°-178° C.

Workup

  1. customprepared
  2. filtrationThe solid was collected by filtration
  3. washwashed

Sources & evidence

ORD record
ord-efe195ecb64341ab98f8a4f31a0d181a
Source dataset
uspto-grants-1987_12
Patent number
US04715993

Reaction notes

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