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

HRID 861201Notes

Reaction equation

HRID 861201 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>[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

4

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 85.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
123 °C

Procedure

To 300 g of polyphosphoric acid (112% phosphoric acid) heated at 88° C. was added 0.07 g of N-[3-(N,N-dimethylaminopropyl)] copper phthalocyanine sulfonamide followed by 68.2 g of 2,5-di(4-methylanilino)terephthalic acid added over a period of 35 minutes, the temperature being maintained below 120° C. by adjustment of the addition rate. The mixture was heated at 123° C. for two hours. After the melt was cooled to 93° C., it was slowly poured into 500 g of methanol, the temperature being maintained below 64° C. by external cooling and adjustment of melt addition rate. The slurry was heated at reflux for one hour, cooled to below 60° C., diluted with water, filtered, and washed until acid free. The resultant presscake was reslurried in water. After adjustment of the pH to greater than 7, 5.5 g of 50% sodium hydroxide was added and the resultant slurry was heated at 90° C. for one hour. The slurry was cooled, filtered, and washed with water until alkali free, then reslurried in water. After adjustment of the pH to 9.5, the slurry was heated at 143° C. for two hours in a closed system (e.g., a pressure reactor), and cooled to 40° C. After the slurry was acidified to pH 3.3, an emulsion of 2.2 g of an anionic surfactant, 30 g of a petroleum distillate, and 80 g of water was added, and the slurry was stirred for three hours. The solid component was collected by filtration and washed with water. The wet cake was dried in an oven at 60° C. to give approximately 53 g of 2,9-dimethylquinacridone as a magenta pigment.

Workup

  1. additionadded over a period of 35 minutes
  2. temperaturethe temperature being maintained below 120° C. by adjustment of the addition rate
  3. temperatureAfter the melt was cooled to 93° C.
  4. temperaturethe temperature being maintained below 64° C.
  5. temperatureby external cooling
  6. additionadjustment of melt addition rate
  7. temperatureThe slurry was heated
  8. temperatureat reflux for one hour
  9. temperaturecooled to below 60° C.
  10. filtrationfiltered
  11. washwashed until acid free
  12. additionAfter adjustment of the pH to greater than 7, 5.5 g of 50% sodium hydroxide was added
  13. temperaturethe resultant slurry was heated at 90° C. for one hour
  14. temperatureThe slurry was cooled
  15. filtrationfiltered
  16. washwashed with water until alkali free,
  17. temperatureAfter adjustment of the pH to 9.5, the slurry was heated at 143° C. for two hours in a closed system (e.g., a pressure reactor)
  18. temperaturecooled to 40° C
  19. additionan emulsion of 2.2 g of an anionic surfactant, 30 g of a petroleum distillate, and 80 g of water was added
  20. filtrationThe solid component was collected by filtration
  21. washwashed with water
  22. customThe wet cake was dried in an oven at 60° C.

Sources & evidence

ORD record
ord-0d517a2485134e238acf0e0b147c93aa
Source dataset
uspto-grants-1998_02
Patent number
US05713999

Reaction notes

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