Ammonia → Mitoxantrone

HRID 477419Notes

Reaction equation

HRID 477419 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 (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 stirred at 0° C. for one hour with the continuous slow addition of ammonia gas. The solid was collected and washed by slurrying with five 150 ml portions of ammonia saturated methanol, giving 22.9 g of 1,4-dihydroxy-5,8-bis[[2-(2-hydroxyethylamino)ethyl]amino]anthraquinone free base as blue-black microrods, mp 175°-178° C.

Workup

  1. customThe solid was collected
  2. washwashed

Sources & evidence

ORD record
ord-7ed3049ffe1d4927ad2b0625bab4ca3a
Source dataset
uspto-grants-1989_12
Patent number
US04888137

Reaction notes

Loading…