Sodium Hydroxide → 1-Amino-4-bromoanthraquinone

HRID 2419233

Reaction equation

HRID 2419233 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[C:5]([Br:18])=[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[C:5]([Br:18])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24489Sodium DithioniteHCID 2715931-Amino-4-bromo-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid

Product 1

HCID 6273261-Amino-4-bromoanthraquinoneYield 75%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1-Amino-4-bromoanthraquinone-2-carboxylic acid (38 grams, 0.11 mole) was dissolved in 200 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 (b 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 resuting solid was collected by filtration and washed with water until the filtrate was neutral. The solid was dried at 80° C. to give 24.9 g (75% yield) of 1-amino-4-bromoanthraquinone. The Thin Layer Chromatogram of the crude product showed the presence of a small amount of impurity.

Workup

  1. temperatureThe mixture was heated on a steam bath to 90°-100° C.
  2. temperatureHeating
  3. filtrationThe resuting 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-ff9c3a58ec4e4e8ea7fef280aa9e2e86
Source dataset
uspto-grants-1978_08
Patent number
US04105680

Linked notes

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