Sodium Hydroxide → Quinacridone

HRID 976122Notes

Reaction equation

HRID 976122 reaction equation
[OH-].[Na+].[CH2:3]1[C:8]2[NH:9][C:10]3[C:15]([C:16](=[O:17])[C:7]=2[CH2:6][C:5]2[NH:18][C:19]4[C:24]([C:25](=[O:26])[C:4]1=2)=[CH:23][CH:22]=[CH:21][CH:20]=4)=[CH:14][CH:13]=[CH:12][CH:11]=3.[N+](C1C=C(S([O-])(=O)=O)C=CC=1)([O-])=O.[Na+]>CO>[CH:22]1[CH:23]=[C:24]2[C:25]([C:4]3[C:5]([NH:18][C:19]2=[CH:20][CH:21]=1)=[CH:6][C:7]1[C:16]([C:15]2[C:10]([NH:9][C:8]=1[CH:3]=3)=[CH:11][CH:12]=[CH:13][CH:14]=2)=[O:17])=[O:26]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 31389Sodium 3-nitrobenzenesulfonateHCID 79973Quino(2,3-b)acridine-7,14-dione, 5,6,12,13-tetrahydro-

Product 1

HCID 13976Quinacridone

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

79 Parts of methanol and 12 parts of a 50% NaOH aqueous solution were fully stirred in a stainless steel flask having a refluxing device. 10 Parts of the 6,13-dihydroquinacridone obtained in Example 1 and 10 parts of sodium m-nitrobenzenesulfonate were gradually mixed with the above-prepared solution, and the mixture was refluxed at 70° to 75° C. for 3 to 5 hours. The reaction mixture was cooled to 40° C. and filtered, and the resultant cake was cleaned with hot water until a wash liquid became colorless and transparent, to give 9.77 parts (98.3% of a theoretical value) of a nonsubstituted quinacridone. The so-obtained quinacridone was measured by IR and absorbance to show 99.2% of quinacridone and 0.8% of 6,13-dihydroquinacridone. The quinacridone had a specific surface area of 22.1 m2 /g.

Workup

  1. temperaturethe mixture was refluxed at 70° to 75° C. for 3 to 5 hours
  2. filtrationfiltered

Sources & evidence

ORD record
ord-7a6cb096bbc042858e95bb8fa78f4e12
Source dataset
uspto-grants-1997_03
Patent number
US05610306

Reaction notes

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