2,5-Di-p-toluidinoterephthalic acid → 5,12-Dihydro-2,9-dimethylquino(2,3-b)acridine-7,14-dione

HRID 378534

Reaction equation

[C:1]1([CH3:28])[CH:6]=[CH:5][C:4]([NH:7][C:8]2[CH:16]=[C:15]([C:17]([OH:19])=O)[C:14]([NH:20][C:21]3[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=3)=[CH:13][C:9]=2[C:10](O)=[O:11])=[CH:3][CH:2]=1>O>[CH3:27][C:24]1[CH:23]=[CH:22][C:21]2[NH:20][C:14]3[C:15]([C:17](=[O:19])[C:26]=2[CH:25]=1)=[CH:16][C:8]1[NH:7][C:4]2[CH:3]=[CH:2][C:1]([CH3:28])=[CH:6][C:5]=2[C:10](=[O:11])[C:9]=1[CH:13]=3

Participants

Conditions

Temperature: 130 °C

Procedure

To 150.0 g of polyphosphoric acid (118%) was added with stirring 30.0 g (79.7 mmol) of 2,5-bis(p-toluidino)terephthalic acid. The stirred mixture was irradiated in the microwave oven for 2.5 minutes. After the reaction mixture was cooled to 130° C., 250 g of water was slowly added with stirring. The resultant slurry was stirred for 30 minutes, after which the solid component was collected by filtration and washed with 6.0 liters of water. The presscake was dried overnight in an oven at 60° C. to give 27.0 g of crude 2,9-dimethylquinacridone (C. I. Pigment Red 122) (100% yield).

Workup

customThe stirred mixture was irradiated in the microwave oven for 2.5 minutes
stirringThe resultant slurry was stirred for 30 minutes
filtrationafter which the solid component was collected by filtration
washwashed with 6.0 liters of water
customThe presscake was dried overnight in an oven at 60° C.

Sources & evidence

ORD record: ord-b45aaa79961e4e3fa4ac0b9d300f449d
Source dataset: uspto-grants-2000_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06031100

Linked notes

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