Hydrogen Peroxide → Quinacridone

HRID 1976280Notes

Reaction equation

HRID 1976280 reaction equation
[CH2:1]1[C:6]2[NH:7][C:8]3[C:13]([C:14](=[O:15])[C:5]=2[CH2:4][C:3]2[NH:16][C:17]4[C:22]([C:23](=[O:24])[C:2]1=2)=[CH:21][CH:20]=[CH:19][CH:18]=4)=[CH:12][CH:11]=[CH:10][CH:9]=3.CO.[OH-].[Na+].OO>C1C2C(=O)C3C(=CC=CC=3)C(=O)C=2C=CC=1.O>[CH:20]1[CH:21]=[C:22]2[C:23]([C:2]3[C:3]([NH:16][C:17]2=[CH:18][CH:19]=1)=[CH:4][C:5]1[C:14]([C:13]2[C:8]([NH:7][C:6]=1[CH:1]=3)=[CH:9][CH:10]=[CH:11][CH:12]=2)=[O:15])=[O:24]

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 887MethanolHCID 14798Sodium HydroxideHCID 79973Quino(2,3-b)acridine-7,14-dione, 5,6,12,13-tetrahydro-

Product 1

HCID 13976QuinacridoneYield 97.9%

Reagents, catalysts & solvents 2

HCID 6780AnthraquinoneCatalystHCID 962WaterSolvent

Conditions

Temperature
52.5 °C

Procedure

A one liter flask equipped with a thermometer, stirrer and condenser was charged with 40 grams 6,13-dihydroquinacridone, 185 ml methanol, 42 grams 50% aqueous sodium hydroxide and 1.2 grams of the barbituric acid methyl dihydro-quinacridone additive prepared according to Example 3. The mixture was stirred under a slow flow of nitrogen at 50 to 55° C. for one hour. 0.5 gram anthraquinone mono sulfonic acid sodium salt, as catalyst, was added and the reaction mixture was heated to reflux. 67 grams of an aqueous 19.3% hydrogen peroxide solution were added into the reaction mixture with a peristaltic pump at a pumping rate of 0.3 ml/minute while maintaining reflux and a slow nitrogen flow. The resulting violet suspension was further stirred for 10 minutes at reflux, then diluted with 100 ml cold water and filtered. The presscake was washed with hot water then dried, yielding 38.9 grams violet reddish quinacridone.

Workup

  1. customA one liter flask equipped with a thermometer, stirrer and condenser
  2. customprepared
  3. temperaturethe reaction mixture was heated to reflux
  4. temperaturewhile maintaining
  5. temperaturereflux
  6. stirringThe resulting violet suspension was further stirred for 10 minutes
  7. temperatureat reflux
  8. filtrationfiltered
  9. washThe presscake was washed with hot water
  10. customthen dried

Sources & evidence

ORD record
ord-fbd4828653244bd6b40e3b5345c207ee
Source dataset
uspto-grants-2001_05
Patent number
US06225472B1

Reaction notes

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