Sulfate Ion → 1-Hydroxy-5-[(1-methylethyl)amino]-9,10-anthracenedione

HRID 918539Notes

Reaction equation

HRID 918539 reaction equation
S(=O)(=O)(O)O.[CH:6]([NH:9][C:10]1[C:23]2[C:22](=[O:24])[C:21]3[C:16](=[C:17]([O:25]C)[CH:18]=[CH:19][CH:20]=3)[C:15](=[O:27])[C:14]=2[CH:13]=[CH:12][CH:11]=1)([CH3:8])[CH3:7].S([O-])([O-])(=O)=O>O>[CH:6]([NH:9][C:10]1[C:23]2[C:22](=[O:24])[C:21]3[C:16](=[C:17]([OH:25])[CH:18]=[CH:19][CH:20]=3)[C:15](=[O:27])[C:14]=2[CH:13]=[CH:12][CH:11]=1)([CH3:8])[CH3:7]

Participants

5

Reactant 3

HCID 1117Sulfate IonHCID 1118Sulfuric AcidHCID 215211761-Methoxy-5-[(1-methylethyl)amino]-9,10-anthracenedione

Product 1

HCID 215211751-Hydroxy-5-[(1-methylethyl)amino]-9,10-anthracenedioneYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

This press cake is introduced with intensive stirring into 34.7 parts of 90% strength sulphuric acid, the solution is warmed to 120°-125° until no further 1-isopropylamino-5-methoxy-anthraquinone is chromatographically detectable in a worked-up sample (about 3 hours are required) and is diluted with 18 parts of water at 50°-80°, the mixture is stirred overnight in the cold, and the sulphate which has precipitated in large boat-shaped plates is filtered off, washed with 50% strength sulphuric acid, decomposed with water, and the product washed until neutral and dried. 12.9 parts (90% of theory) of 1-isopropylamino-5-hydroxy-anthraquinone are obtained.

Workup

  1. additionThis press cake is introduced
  2. customis chromatographically detectable in a worked-up sample (about 3 hours are required)
  3. customhas precipitated in large boat-shaped plates
  4. filtrationis filtered off
  5. washwashed with 50% strength sulphuric acid
  6. washthe product washed until neutral and
  7. customdried

Sources & evidence

ORD record
ord-bfe73126ee5e4422be088a798ca46b17
Source dataset
uspto-grants-1976_07
Patent number
US03971812

Reaction notes

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