2,5-Dianilinoterephthalic acid → 3-Acridinecarboxylic acid, 9,10-dihydro-9-oxo-2-(phenylamino)-

HRID 463801

Reaction equation

HRID 463801 reaction equation
[C:1]1([NH:7][C:8]2[CH:16]=[C:15]([C:17](O)=[O:18])[C:14]([NH:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:13][C:9]=2[C:10]([OH:12])=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>P(=O)(O)(O)O>[C:1]1([NH:7][C:8]2[C:9]([C:10]([OH:12])=[O:11])=[CH:13][C:14]3[NH:20][C:21]4[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=4)[C:17](=[O:18])[C:15]=3[CH:16]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 1

HCID 823512,5-Dianilinoterephthalic acid

Product 1

HCID 110674753-Acridinecarboxylic acid, 9,10-dihydro-9-oxo-2-(phenylamino)-

Reagents, catalysts & solvents 1

HCID 1004Phosphoric AcidSolvent

Procedure

A process is disclosed wherein 2,5-di(phenylamino) terephthalic acid is half-cyclized by dissolving it in a mixture of polyphosphoric acid and phosphoric acid and heating at 100°-120° C. to form 2-(phenyl)amino-3-carboxy-9(10H)acridone (ACA). The ACA is decarboxylated to form 2-(phenyl)amino-9(10H)acridone, also known as 2-anilinoacridone, by dissolving it in tetramethylene sulfone and heating in the presence of a basic cupric carbonate catalyst.

Workup

  1. dissolutionby dissolving it
  2. temperatureheating at 100°-120° C.

Sources & evidence

ORD record
ord-841256f29c574e16a8539eaeb3b9e9bd
Source dataset
uspto-grants-1985_10
Patent number
US04544746

Linked notes

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