Water → Quino[2,3-b]acridine-7,14-dione, 2,9-dichloro-5,12-dihydro-

HRID 378536

Reaction equation

[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([NH:6][C:7]2[CH:15]=[C:14]([C:16]([OH:18])=O)[C:13]([NH:19][C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=3)=[CH:12][C:8]=2[C:9]([OH:11])=O)=[CH:4][CH:3]=1.O>CO>[CH:3]1[C:2]([Cl:1])=[CH:28][C:27]2[C:9]([C:8]3[C:7]([NH:6][C:5]=2[CH:4]=1)=[CH:15][C:14]1[C:16]([C:21]2[CH:22]=[C:23]([Cl:26])[CH:24]=[CH:25][C:20]=2[NH:19][C:13]=1[CH:12]=3)=[O:18])=[O:11]

Participants

Conditions

Temperature: 150 °C

Procedure

To 200.0 g of polyphosphoric acid (118%) were added 30.0 g (71.7 mmol) of 2,5-bis(p-chloroanilino)terephthalic acid and 0.6 g of phthalimidomethylquinacridone. The stirred mixture was irradiated in the microwave oven for 2.0 minutes. The reaction mixture was cooled to 150° C. and drowned in 400 g of methanol with vigorous stirring. The resultant methanol suspension was maintained at reflux for one hour, cooled to 60° C., added to 800 g of water, and heated at 60° C. for 30 minutes. The solid component was collected by filtration and washed with 8.0 liters of water. The presscake was dried overnight in an oven at 60° C. to give 28.0 g of 2,9-dichloroquinacridone (C. I. Pigment Red 202).

Workup

customThe stirred mixture was irradiated in the microwave oven for 2.0 minutes
temperatureat reflux for one hour
temperaturecooled to 60° C.
temperatureheated at 60° C. for 30 minutes
filtrationThe solid component was collected by filtration
washwashed with 8.0 liters of water
customThe presscake was dried overnight in an oven at 60° C.

Sources & evidence

ORD record: ord-54095886937a44aabe8a9399fd926fcb
Source dataset: uspto-grants-2000_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06031100

Linked notes

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