Phenolate → 4-Amino-6-chloro-1-hydroxy-2-phenoxyanthracene-9,10-dione

HRID 1789321Notes

Reaction equation

HRID 1789321 reaction equation
[OH:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][C:10]([Cl:17])=[CH:11][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][C:10]([Cl:17])=[CH:11][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 20188059HCID 20188059, compound

Product 1

HCID 201880714-Amino-6-chloro-1-hydroxy-2-phenoxyanthracene-9,10-dione

Procedure

When 70.5 g of the 1-hydroxy-2-bromo-4-amino-6-chloroanthraquinone prepared above are subjected to a phenolate fusion as described in Example 467c, then 59 g, corresponding to 80% of theory, of 1-hydroxy-2-phenoxy-4-amino-6-chloroanthraquinone are obtained, the colour shade of which on silica gel is a pink tinged with blue having the Indicator Number 51 (Colour Index Hue Indication Chart).

Sources & evidence

ORD record
ord-3b0a368a26d1420fa70558b211b82b38
Source dataset
uspto-grants-1987_08
Patent number
US04689171

Reaction notes

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