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

HRID 2298708Notes

Reaction equation

HRID 2298708 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.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>[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

7

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 102.2%

Reagents, catalysts & solvents 3

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

Conditions

Temperature
94 °C

Procedure

To 900 g of polyphosphoric acid (116.5%) heated at 90° C. were added 3.0 g of 2,5-di(sulfamoylanilino)terephthalic acid followed by 7.5 g of 2,5-di[4-(N,N-diethylsulfamoyl)anilino]terephthalic acid. The mixture was stirred for five minutes, after which 150 g of 2,5-di(4-chloroanilino)terephthalic acid were added over a period of approximately 45 minutes, the temperature being maintained below 115° C. by adjustment of the addition rate. The reaction mixture was held at 113° C. for four hours and then cooled to 94° C. To this mixture was added 110.2 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 1550 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 140 g of 2,9-dichloroquinacridone as a magenta pigment. A portion of the pigment was used to prepare a blend containing 90% by weight of the pigment and 10% by weight of phthalimidomethylquinacridone.

Workup

  1. temperaturethe temperature being maintained below 115° C. by adjustment of the addition rate
  2. waitThe reaction mixture was held at 113° C. for four hours
  3. stirringto stir for 15 minutes at 92° C.
  4. temperaturethe temperature being maintained
  5. temperaturebelow reflux by adjustment of the addition rate
  6. temperatureto cool to room temperature
  7. waitstand for 16 hours
  8. temperatureThe pigment slurry was heated
  9. temperatureat reflux for one hour
  10. temperaturecooled below 65° C.
  11. filtrationcollected by filtration
  12. washwashed with water until free of acid
  13. customThe resultant wet cake can be dried
  14. customHere, the wet cake was dried in an oven at 60° C.

Sources & evidence

ORD record
ord-4091b0b7e14a4d9c94142cd59e9d5113
Source dataset
uspto-grants-2002_12
Patent number
US06494948B2

Reaction notes

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