2-Anthracenecarboxylic acid, 1-amino-9,10-dihydro-9,10-dioxo- → 1-Aminoanthraquinone

HRID 2419231Notes

Reaction equation

HRID 2419231 reaction equation
[NH2:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:17])[C:6]=2[CH:5]=[CH:4][C:3]=1C(O)=O.[OH-].[Na+].S(S([O-])=O)([O-])=O.[Na+].[Na+]>O>[NH2:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 67012-Anthracenecarboxylic acid, 1-amino-9,10-dihydro-9,10-dioxo-HCID 14798Sodium HydroxideHCID 24489Sodium Dithionite

Product 1

HCID 67101-AminoanthraquinoneYield 78%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The wet cake of 1-aminoanthraquinone-2-carboxylic acid was dissolved in 2000 ml. of water and 50 ml. of 10 M sodium hydroxide solution. The mixture was heated on a steam bath to 90°-100° C. and 40 g (0.23 mole) sodium hydrosulfite was added. Heating was continued with stirring for 2 hours, after which the mixture was cooled to room temperature. The resulting red solid was collected by filtration and washed with water until the filtrate was neutral. The solid was dried at 80° C. to give 19.5 g (78% yield) of 1-aminoanthraquinone. The Thin Layer Chromatogram of the crude product showed the presence of less than 5% of impurity.

Workup

  1. temperatureThe mixture was heated on a steam bath to 90°-100° C.
  2. temperatureHeating
  3. filtrationThe resulting red solid was collected by filtration
  4. washwashed with water until the filtrate
  5. customThe solid was dried at 80° C.

Sources & evidence

ORD record
ord-e79ecc6f79e5417b97adc8bbc60ec744
Source dataset
uspto-grants-1978_08
Patent number
US04105680

Reaction notes

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