Phenolate → 4-Amino-7-chloro-1-hydroxy-2-phenoxyanthracene-9,10-dione

HRID 1789322Notes

Reaction equation

HRID 1789322 reaction equation
[OH:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[C:11]([Cl:17])[CH:12]=3)[C:7](=[O:18])[C:6]=2[C:5]([NH2:19])=[CH:4][C:3]=1Br.[C:21]1([O-:27])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>>[OH:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[C:11]([Cl:17])[CH:12]=3)[C:7](=[O:18])[C:6]=2[C:5]([NH2:19])=[CH:4][C:3]=1[O:27][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

3

Reactant 2

HCID 119047PhenolateHCID 201880524-Amino-2-bromo-7-chloro-1-hydroxy-9,10-anthracenedione

Product 1

HCID 201880654-Amino-7-chloro-1-hydroxy-2-phenoxyanthracene-9,10-dione

Procedure

When 70.5 g of the 1-hydroxy-2-bromo-4-amino-7-chloroanthraquinone prepared above are subjected to a phenolate fusion as described in Example 467c, then 61 g, corresponding to 83% of theory, of 1-hydroxy-2-phenoxy-4-amino-7-chloro-anthraquinone are obtained, the colour shade of which on silica gel is a pink tinged with blue having the Indicator Number of 51 (Colour Index Hue Indication Chart).

Sources & evidence

ORD record
ord-a983ac3eee2e42748e865bdbd507ab4d
Source dataset
uspto-grants-1987_08
Patent number
US04689171

Reaction notes

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