Hydrogen Peroxide → Quinacridone

HRID 1168654Notes

Reaction equation

HRID 1168654 reaction equation
C1(C=CC(O)=CC=1)O.OO.[CH2:11]1[C:16]2[NH:17][C:18]3[C:23]([C:24](=[O:25])[C:15]=2[CH2:14][C:13]2[NH:26][C:27]4[C:32]([C:33](=[O:34])[C:12]1=2)=[CH:31][CH:30]=[CH:29][CH:28]=4)=[CH:22][CH:21]=[CH:20][CH:19]=3>>[CH:30]1[CH:31]=[C:32]2[C:33]([C:12]3[C:13]([NH:26][C:27]2=[CH:28][CH:29]=1)=[CH:14][C:15]1[C:24]([C:23]2[C:18]([NH:17][C:16]=1[CH:11]=3)=[CH:19][CH:20]=[CH:21][CH:22]=2)=[O:25])=[O:34]

Participants

4

Reactant 3

HCID 784Hydrogen PeroxideHCID 785HydroquinoneHCID 79973Quino(2,3-b)acridine-7,14-dione, 5,6,12,13-tetrahydro-

Product 1

HCID 13976Quinacridone

Procedure

While the hydroquinone assisted hydrogen peroxide oxidation of 6,13-dihydroquinacridone produces a gamma-I quinacridone, surprisingly a combination of hydroquinone and pyrazolylmethyl quinacridone generates a gamma-II quinacridone. It is further surprising that the oxidation of 6,13-dihydroquinacridone in the presence of 2-naphthol creates a gamma-III quinacridone.

Sources & evidence

ORD record
ord-d1c55c3b0fd3493cb75f592396e77514
Source dataset
uspto-grants-2003_09
Patent number
US06626990B2

Reaction notes

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