Isobutylamine → HCID 21512169, compound

HRID 1576347Notes

Reaction equation

HRID 1576347 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[C:8](Br)=[CH:7][CH:6]=1)([CH3:3])[CH3:2].[CH2:23]([NH2:27])[CH:24]([CH3:26])[CH3:25]>CO.[Cu]Cl.S([O-])([O-])(=O)=O.[Cu+2]>[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]([NH:27][CH2:23][CH:24]([CH3:26])[CH3:25])=[CH:7][CH:6]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 2

HCID 6558IsobutylamineHCID 215121524-Bromo-5-hydroxy-1-[(1-methylethyl)amino]-9,10-anthracenedione

Product 1

HCID 21512169HCID 21512169, compound

Reagents, catalysts & solvents 3

HCID 24462Copper SulfateCatalystHCID 62652Cuprous chlorideCatalystHCID 887MethanolSolvent

Procedure

10 Parts 1-isopropylamino-4-bromo-5-hydroxy-anthraquinone, 50 parts isobutylamine, 0.1 part each of copper(I) chloride and basic copper sulphate are boiled under reflux (appr. 70°) until only small amounts of starting material can be detected (appr. 2 hours are required). The mixture is diluted with 50 parts methanol, the precipitated needles are filtered off with suction in the cold, washed with methanol and hot water. It is also possible to filter off with suction without previous dilution with methanol. The 1-isopropylamino-5-hydroxy-4-isobutylamino-anthraquinone so obtained is sulphonated as follows:

Workup

  1. temperatureunder reflux (appr. 70°) until only small amounts of starting material
  2. custom(appr. 2 hours are required)
  3. filtrationthe precipitated needles are filtered off with suction in the cold
  4. washwashed with methanol and hot water
  5. filtrationto filter off with suction without previous dilution with methanol

Sources & evidence

ORD record
ord-ca7141dec83d42a4928ee4c65c50480e
Source dataset
uspto-grants-1976_09
Patent number
US03980677

Reaction notes

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