5-Nitro-1,4,4a,9a-tetrahydroanthraquinone → 1-Amino-6,7-dimethylanthracene-9,10-dione

HRID 622324Notes

Reaction equation

HRID 622324 reaction equation
[N+](C1C=CC=C2C=1C(=O)C1C(C2=O)CC=CC1)([O-])=O.[N+:20]([C:23]1[CH:36]=[CH:35][CH:34]=[C:33]2[C:24]=1[C:25](=[O:40])[CH:26]1[CH:31]([C:32]2=[O:37])[CH2:30][C:29]([CH3:38])=[C:28]([CH3:39])[CH2:27]1)([O-])=O>>[NH2:20][C:23]1[C:24]2[C:25](=[O:40])[C:26]3[C:31](=[CH:30][C:29]([CH3:38])=[C:28]([CH3:39])[CH:27]=3)[C:32](=[O:37])[C:33]=2[CH:34]=[CH:35][CH:36]=1

Participants

3

Reactant 2

HCID 108689405-Nitro-1,4,4a,9a-tetrahydroanthraquinoneHCID 212925545-Nitro-2,3-dimethyl-1,4,4a,9a-tetrahydroanthraquinone

Product 1

HCID 212925531-Amino-6,7-dimethylanthracene-9,10-dioneYield 99%

Procedure

The process of Example 1 is repeated, replacing 64.3 parts of 5-nitro-1,4,4a,9a-tetrahydroanthraquinone by 71.3 parts of 5-nitro-2,3-dimethyl-1,4,4a,9a-tetrahydroanthraquinone (obtained from 1-nitronaphthoquinone and 2,3-dimethyl-1,4-butadiene by Diels-Alder reaction), to give 61.9 parts of 1-amino-6,7-dimethylanthraquinone in 99% purity, corresponding to a yield of 99% of theory.

Sources & evidence

ORD record
ord-523715f226624d8faab37a9541c985ab
Source dataset
uspto-grants-1988_09
Patent number
US04770818

Reaction notes

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