Methanol → 5,12-Dihydro-2,9-dimethylquino(2,3-b)acridine-7,14-dione

HRID 2298714Notes

Reaction equation

HRID 2298714 reaction equation
[CH3:1][C:2]1[CH:28]=[CH:27][C:5]([NH:6][C:7]2[CH:15]=[C:14]([C:16]([OH:18])=O)[C:13]([NH:19][C:20]3[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=3)=[CH:12][C:8]=2[C:9](O)=[O:10])=[CH:4][CH:3]=1.CO>O.S(N(C1C=C(C(O)=O)C(N(S(=O)(=O)N)C2C=CC=CC=2)=CC=1C(O)=O)C1C=CC=CC=1)(=O)(=O)N.C(N(CC)S(C1C=CC(NC2C=C(C(O)=O)C(NC3C=CC(S(=O)(=O)N(CC)CC)=CC=3)=CC=2C(O)=O)=CC=1)(=O)=O)C>[CH3:1][C:2]1[CH:28]=[CH:27][C:5]2[NH:6][C:7]3[C:8]([C:9](=[O:10])[C:4]=2[CH:3]=1)=[CH:12][C:13]1[NH:19][C:20]2[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][C:21]=2[C:16](=[O:18])[C:14]=1[CH:15]=3

Participants

6

Reactant 2

HCID 887MethanolHCID 825242,5-Di-p-toluidinoterephthalic acid

Product 1

HCID 704235,12-Dihydro-2,9-dimethylquino(2,3-b)acridine-7,14-dioneYield 104.4%

Reagents, catalysts & solvents 3

HCID 18377739HCID 18377739, compoundCatalystHCID 18377742HCID 18377742, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
93 °C

Procedure

To 720 g of polyphosphoric acid (112%) heated at 85° C. were added 1.6 g of 2,5-di(sulfamoylanilino)terephthalic acid followed by 8 g of 2,5-di[4-(N,N-diethylsulfamoyl)anilino]terephthalic acid. The mixture was stirred for five minutes, after which 160 g of 2,5-di(4-methylanilino)terephthalic acid were added over a period of approximately 65 minutes, the temperature being maintained below 110° C. by adjustment of the addition rate. The reaction mixture was held at 123° C. for two hours, cooled to 93° C., and poured slowly into 1120 g of methanol, the temperature being maintained below reflux using a water bath. The pigment slurry was heated at reflux for one hour, cooled below 65° C., diluted with water, collected by filtration, and washed with water until free of acid. The resultant presscake was reslurried in water and heated to 45° C. After the slurry was acidified to pH 2.5, an emulsion of 4.7 g of an anionic surfactant, 69.6 g of a petroleum distillate, and 160 g of water was added, and the slurry was stirred for three hours. The resultant slurry was collected by filtration and washed with water. The wet cake can be dried or used as is for specific applications. Here, the wet cake was dried in an oven at 60° C. to give approximately 151 g of 2,9-dimethylquinacridone as a magenta pigment.

Workup

  1. temperaturethe temperature being maintained below 110° C. by adjustment of the addition rate
  2. waitThe reaction mixture was held at 123° C. for two hours
  3. temperaturethe temperature being maintained
  4. temperaturebelow reflux
  5. temperatureThe pigment slurry was heated
  6. temperatureat reflux for one hour
  7. temperaturecooled below 65° C.
  8. filtrationcollected by filtration
  9. washwashed with water until free of acid
  10. temperatureheated to 45° C
  11. additionan emulsion of 4.7 g of an anionic surfactant, 69.6 g of a petroleum distillate, and 160 g of water was added
  12. stirringthe slurry was stirred for three hours
  13. filtrationThe resultant slurry was collected by filtration
  14. washwashed with water
  15. customThe wet cake can be dried
  16. customHere, the wet cake was dried in an oven at 60° C.

Sources & evidence

ORD record
ord-3861c5e7b8ef471eb844a877b51b8887
Source dataset
uspto-grants-2002_12
Patent number
US06494948B2

Reaction notes

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