Bromine → 4-Bromo-5-hydroxy-1-[(1-methylethyl)amino]-9,10-anthracenedione

HRID 918540Notes

Reaction equation

HRID 918540 reaction equation
[CH:1]([NH:4][C:5]1[C:18]2[C:17](=[O:19])[C:16]3[C:11](=[C:12]([OH:20])[CH:13]=[CH:14][CH:15]=3)[C:10](=[O:21])[C:9]=2[CH:8]=[CH:7][CH:6]=1)([CH3:3])[CH3:2].[Br:22]Br>Cl>[CH:1]([NH:4][C:5]1[C:18]2[C:17](=[O:19])[C:16]3[C:11](=[C:12]([OH:20])[CH:13]=[CH:14][CH:15]=3)[C:10](=[O:21])[C:9]=2[C:8]([Br:22])=[CH:7][CH:6]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 24408BromineHCID 215211751-Hydroxy-5-[(1-methylethyl)amino]-9,10-anthracenedione2×

Product 1

HCID 215121524-Bromo-5-hydroxy-1-[(1-methylethyl)amino]-9,10-anthracenedione

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

If the 12.9 parts of 1-isopropylamino-5-hydroxy-anthraquinone obtained in Example 3 are dissolved in 130 parts of 30% strength hydrochloric acid, 9.5 parts of bromine are added dropwise at room temperature, and the mixture is further stirred at room temperature or at elevated temperature (up to 40°) until at most 5% of 1-isopropylamino-5-hydroxy-anthraquinone can still be detected chromatographically in a sample which has been withdrawn, then 15.95 parts of 1-isopropylamino-5-hydroxy-4-bromanthraquinone are obtained after pouring out into 300 parts of water and further working up as described in (a). The quality of this product is only slightly better than that of the product obtained according to Example 4a.

Workup

  1. additionare added dropwise at room temperature
  2. customhas been withdrawn

Sources & evidence

ORD record
ord-c64feda6af1d4e598e5c72bc530e0fcf
Source dataset
uspto-grants-1976_07
Patent number
US03971812

Reaction notes

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