1,4-Cyclohexadiene-1,4-dicarboxylic acid, 2,5-bis(phenylamino)-, 1,4-dimethyl ester → Quino(2,3-b)acridine-7,14-dione, 5,6,12,13-tetrahydro-

HRID 378537

Reaction equation

CO[C:3]([C:5]1[CH2:10][C:9]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:8]([C:18]([O:20]C)=O)[CH2:7][C:6]=1[NH:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:4]>O>[CH2:7]1[C:6]2[NH:22][C:23]3[C:24]([C:3](=[O:4])[C:5]=2[CH2:10][C:9]2[NH:11][C:12]4[C:13]([C:18](=[O:20])[C:8]1=2)=[CH:14][CH:15]=[CH:16][CH:17]=4)=[CH:25][CH:26]=[CH:27][CH:28]=3

Participants

Conditions

Temperature: 80 °C

Procedure

To 120.0 g of polyphosphoric acid (118%) was added with stirring 20.0 g (52.9 mmol) of 2,5-bis(phenylamino)-1,4-cyclohexadiene-1,4-dicarboxylic acid dimethyl ester. The stirred mixture was irradiated in the microwave oven for 1.5 minutes. After the reaction mixture was cooled to 80° C., water was added with stirring. The resultant slurry was stirred for 5 minutes, after which the solid component was collected by filtration and washed with 3.0 liters of water. The presscake was dried overnight in an oven at 60° C. to give 15.9 g of 6,13-dihydroquinacridone (95.7% yield, 97.0% spectroscopic purity).

Workup

customThe stirred mixture was irradiated in the microwave oven for 1.5 minutes
stirringThe resultant slurry was stirred for 5 minutes
filtrationafter which the solid component was collected by filtration
washwashed with 3.0 liters of water
customThe presscake was dried overnight in an oven at 60° C.

Sources & evidence

ORD record: ord-38459cfb6d284f3d8a61d9770f6fbe9f
Source dataset: uspto-grants-2000_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06031100

Linked notes

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