Methanol → 5,12-Dihydroquinolino[2,3-b]acridine-7,14-dione;2,9-dimethyl-5,12-dihydroquinolino[2,3-b]acridine-7,14-dione

HRID 896964Notes

Reaction equation

HRID 896964 reaction equation
C=[CH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:9](O)(=O)C=C.[CH3:14][OH:15].[OH-:16].[K+].C(OOC(=O)CCCCCCC)(=O)CCCCCCC.[CH:38]1[CH:43]=[C:42]2[C:44]([C:46]3[C:51]([NH:52][C:41]2=[CH:40][CH:39]=1)=[CH:50][C:49]1[C:53]([C:55]2[C:60]([NH:61][C:48]=1[CH:47]=3)=[CH:59][CH:58]=[CH:57][CH:56]=2)=[O:54])=[O:45]>CS(C)=O.CC1C=CC2NC3C(C(=O)C=2C=1)=CC1NC2C=CC(C)=CC=2C(=O)C=1C=3.O>[CH:57]1[CH:56]=[C:55]2[C:53]([C:49]3[C:48]([NH:61][C:60]2=[CH:59][CH:58]=1)=[CH:47][C:46]1[C:44]([C:42]2[C:41]([NH:52][C:51]=1[CH:50]=3)=[CH:40][CH:39]=[CH:38][CH:43]=2)=[O:45])=[O:54].[CH3:2][C:3]1[CH:8]=[CH:7][C:6]2[NH:61][C:48]3[C:49]([C:14](=[O:15])[C:5]=2[CH:4]=1)=[CH:50][C:51]1[NH:52][C:41]2[CH:40]=[CH:39][C:38]([CH3:9])=[CH:43][C:42]=2[C:44](=[O:16])[C:46]=1[CH:47]=3

Participants

9

Reactant 5

HCID 887MethanolHCID 12979Caprylyl peroxideHCID 13976Quinacridone2×HCID 14797Potassium HydroxideHCID 22481611Styrene acrylic acid copolymer

Product 1

HCID 1317250385,12-Dihydroquinolino[2,3-b]acridine-7,14-dione;2,9-dimethyl-5,12-dihydroquinolino[2,3-b]acridine-7,14-dione

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent2×HCID 704235,12-Dihydro-2,9-dimethylquino(2,3-b)acridine-7,14-dioneSolvent4×

Conditions

Temperature
0 °C

Procedure

Five parts of a styrene/acrylic acid copolymer (acid value: 250; molecular weight: 5,000) as a dispersing agent were dissolved in 80 parts of dimethyl sulfoxide, and 10 parts of a quinacridone pigment (C.I. Pigment Red 122) were suspended in the resultant solution in a flask at 25° C. under an air atmosphere. A 30% methanol solution of potassium hydroxide was then added dropwise little by little to dissolve the quinacridone pigment. After the pigment solution was stirred for 3 hours, octanoyl peroxide as a polymerization initiator was added to and dissolved in the pigment solution in a proportion of 0.1 parts per 10 parts of the pigment, and the resultant solution was quickly poured into ion-exchanged water (400 parts of ion-exchanged water per 10 parts of the pigment; 0° C.) stirred by an impellor type agitating blade (800 rpm), purged with nitrogen and cooled and temperature-maintained by means of 2 system dispensers (manufactured by Musashi Engineering K.K.; needle internal diameter: 0.57 mm; delivery pressure: 4.0 kgf/cm2) to obtain an aqueous dispersion of quinacridone-pigment-containing particles having an average particle diameter of 35.5 nm. This aqueous dispersion was transferred to a reaction vessel equipped with a mantle heater, cooling tower, stirrer and thermometer. While purging with nitrogen and stirring at 300 rpm, styrene and acrylic acid as ethylenically unsaturated compounds were then added dropwise over 3 hours in proportions of 5.5 parts and 0.5 parts, respectively, per 10 parts of the pigment. The system was then heated to an internal temperature of 80° C. to continue the reaction for 8 hours while retaining the temperature of 80° C. After the reaction was conducted for additional 1 hour at a temperature raised to 90° C., the reaction mixture was cooled back to room temperature.

Workup

  1. stirringagitating blade (800 rpm)
  2. custompurged with nitrogen
  3. temperaturecooled
  4. temperaturetemperature-maintained by means of 2 system dispensers (manufactured by Musashi Engineering K.K.; needle internal diameter: 0.57 mm; delivery pressure: 4.0 kgf/cm2)

Sources & evidence

ORD record
ord-2d7ca6f57d974a658ee2d88cc0e82c5d
Source dataset
uspto-grants-2005_07
Patent number
US06921433B2

Reaction notes

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