Potassium Carbonate → HCID 59514412, compound

HRID 1159353Notes

Reaction equation

HRID 1159353 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6](=[O:24])[N:7]([C:16]3[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][C:17]=3[CH3:23])[C:8](=[O:15])[C:9]3[C:14]=2[C:13]=1[CH:12]=[CH:11][CH:10]=3.C([O-])(=O)C.[K+].C(=O)([O-])[O-].[K+].[K+].Br[C:37]1[CH:46]=[CH:45][C:44]2[N:43]([CH3:47])[C:42](=[O:48])[CH:41]=[C:40]3[C:49]4[C:54]([C:55](=[O:56])[C:38]=1[C:39]=23)=[CH:53][CH:52]=[CH:51][CH:50]=4>CO.ClC1C=CC=CC=1Cl>[CH3:23][C:17]1[CH:18]=[C:19]([CH3:22])[CH:20]=[CH:21][C:16]=1[N:7]1[C:6](=[O:24])[C:5]2[CH:4]=[CH:3][C:2]([NH:1][C:37]3[CH:46]=[CH:45][C:44]4[N:43]([CH3:47])[C:42](=[O:48])[CH:41]=[C:40]5[C:49]6[C:54]([C:55](=[O:56])[C:38]=3[C:39]=45)=[CH:53][CH:52]=[CH:51][CH:50]=6)=[C:13]3[C:14]=2[C:9](=[CH:10][CH:11]=[CH:12]3)[C:8]1=[O:15]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 664923H-Dibenz[f,ij]isoquinoline-2,7-dione, 6-bromo-3-methyl-2×HCID 755891H-Benz[de]isoquinoline-1,3(2H)-dione, 6-amino-2-(2,4-dimethylphenyl)-HCID 517044Potassium Acetate

Product 1

HCID 59514412HCID 59514412, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 72391,2-DichlorobenzeneSolvent2×

Conditions

Temperature
120 °C

Procedure

To a three-necked round-bottomed flask equipped with a thermometer and a Dean-Stark apparatus was charged 6-amino-2-(2,4-dimethylphenyl)benzo[de]isoquinoline-1,3-dione (4.69 g), potassium acetate (1.443 g), potassium carbonate (2.032 g), cupric acetate (0.1262 g), cupric iodide (0.120 g), and ortho-dichlorobenzene (45 ml) to obtain a mixture. The mixture was heated to 120° C. in about 10 minutes. After being maintained at 120° C. for about 30 minutes, 6-bromo-3-methyl-3H-naphtho[1,2,3-de]quinoline-2,7-dione (5 g) and ortho-dichlorobenzene (45 ml) were added to the mixture. Then the temperature of the resulting reaction mixture was raised to 165° C. over a period of about 1.5 hours. After being maintained at this temperature for about 4 hours, formation of a red solid was observed. A portion of the reaction mixture was spotted on a TLC plate and viewed under ultraviolet radiation to monitor the disappearance of the starting materials 6-amino-2-(2,4-dimethyl)phenyl-benzo[de]isoquinoline-1,3-dione and 6-bromo-3-methyl-3H-naphtho[1,2,3-de]quinoline-2,7-dione. After being heated for 2 more hours at the same temperature, TLC analysis of the reaction mixture indicated the absence of both the starting materials. The reaction mixture was then cooled, poured into 175 ml of methanol, filtered, and the filter cake was washed with 2 to 3 100 ml portions of methanol to give the desired product in a yield of 7.2 g.

Workup

  1. customTo a three-necked round-bottomed flask equipped with a thermometer
  2. customto obtain a mixture
  3. temperatureAfter being maintained at 120° C. for about 30 minutes
  4. customThen the temperature of the resulting reaction mixture
  5. temperaturewas raised to 165° C. over a period of about 1.5 hours
  6. temperatureAfter being maintained at this temperature for about 4 hours
  7. temperatureAfter being heated for 2 more hours at the same temperature, TLC analysis of the reaction mixture
  8. temperatureThe reaction mixture was then cooled
  9. filtrationfiltered
  10. washthe filter cake was washed with 2 to 3 100 ml portions of methanol

Sources & evidence

ORD record
ord-bb5fd504559843728d1b246842937900
Source dataset
uspto-grants-2010_10
Patent number
US07812076B2

Reaction notes

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