1,4-Benzenedicarboxylic acid, 2,5-bis[(4-chlorophenyl)amino]- → Quino[2,3-b]acridine-7,14-dione, 2,9-dichloro-5,12-dihydro-

HRID 2056969Notes

Reaction equation

HRID 2056969 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[CH:17]=[C:16]([C:18](O)=[O:19])[C:15]([NH:21][C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=3)=[CH:14][C:10]=2[C:11](O)=[O:12])=[CH:4][CH:3]=1>O>[CH:3]1[C:2]([Cl:1])=[CH:7][C:6]2[C:11]([C:10]3[C:9]([NH:8][C:5]=2[CH:4]=1)=[CH:17][C:16]1[C:18]([C:27]2[CH:26]=[C:25]([Cl:28])[CH:24]=[CH:23][C:22]=2[NH:21][C:15]=1[CH:14]=3)=[O:19])=[O:12]

Participants

3

Reactant 1

HCID 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 101.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2,5-Bis{(4-chlorophenyl)amino}terephthalic acid (3.35 gm; 8 mmol) and polyphosphoric acid (30 gm) were heated at 150° C. for 3 hours under a nitrogen atmosphere. The mixture was allowed to cool and then poured into iced water (200 ml) when a magenta solid precipitated out. This was filtered off, washed with water and methanol, then dried under vacuum over phosphorous pentoxide to give 3.1 gm (100%) of 2,9-dichloroquinacridone.

Workup

  1. temperatureto cool
  2. customprecipitated out
  3. filtrationThis was filtered off
  4. washwashed with water and methanol
  5. dry with materialdried under vacuum over phosphorous pentoxide

Sources & evidence

ORD record
ord-96bf183be74c443cba2045aed49d616e
Source dataset
uspto-grants-2008_02
Patent number
US07335771B2

Reaction notes

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