Methanol → Quino[2,3-b]acridine-7,14-dione, 2,9-dichloro-5,12-dihydro-

HRID 2298704Notes

Reaction equation

HRID 2298704 reaction equation
[Cl: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]([Cl:26])=[CH:22][CH:21]=3)=[CH:12][C:8]=2[C:9]([OH:11])=O)=[CH:4][CH:3]=1.P(=O)(O)(O)O.CO>O>[CH:3]1[C:2]([Cl:1])=[CH:28][C:27]2[C:9]([C:8]3[C:7]([NH:6][C:5]=2[CH:4]=1)=[CH:15][C:14]1[C:16]([C:21]2[CH:22]=[C:23]([Cl:26])[CH:24]=[CH:25][C:20]=2[NH:19][C:13]=1[CH:12]=3)=[O:18])=[O:11]

Participants

5

Reactant 3

HCID 887MethanolHCID 1004Phosphoric AcidHCID 1705571,4-Benzenedicarboxylic acid, 2,5-bis[(4-chlorophenyl)amino]-

Product 1

HCID 76530Quino[2,3-b]acridine-7,14-dione, 2,9-dichloro-5,12-dihydro-Yield 93%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
95 °C

Procedure

To 720 g of polyphosphoric acid (116.5%) heated at 89° C. were added 120 g of 2,5-di(4-chloroanilino)terephthalic acid over a period of approximately 45 minutes, the temperature being maintained below 110° C. by adjustment of the addition rate. The reaction mixture was held at 113° C. for five hours and then cooled to 95° C. To this mixture was added 89.4 g of phosphoric acid (75%) dropwise over a period of 20 minutes. The resultant melt was allowed to stir for 15 minutes at 92° C. and then poured slowly into 1240 g of methanol, the temperature being maintained below reflux by adjustment of the addition rate. The slurry was allowed to cool to room temperature and stand for 16 hours. 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 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 102 g of 2,9-dichloroquinacridone as a magenta pigment.

Workup

  1. temperaturethe temperature being maintained below 110° C. by adjustment of the addition rate
  2. temperaturethe temperature being maintained
  3. temperaturebelow reflux by adjustment of the addition rate
  4. temperatureto cool to room temperature
  5. waitstand for 16 hours
  6. temperatureThe pigment slurry was heated
  7. temperatureat reflux for one hour
  8. temperaturecooled below 65° C.
  9. filtrationcollected by filtration
  10. washwashed with water until free of acid
  11. customThe resultant wet cake can be dried
  12. customHere, the wet cake was dried in an oven at 60° C.

Sources & evidence

ORD record
ord-058f2df9a1c945f6b122302229f6ad0e
Source dataset
uspto-grants-2002_12
Patent number
US06494948B2

Reaction notes

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