Sodium Hydroxide → 1-Amino-4-hydroxyanthraquinone

HRID 2419232

Reaction equation

HRID 2419232 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]([OH:18])=[CH:4][C:3]=1C(O)=O.[OH-].[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]([OH:18])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 38533121-Amino-4-hydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acidHCID 5360545Sodium

Product 1

HCID 83231-Amino-4-hydroxyanthraquinoneYield 99.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1-Amino-4-hydroxyanthraquinone-2-carboxylic acid (31.1 grams, 0.11 mole) 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 hydro ulfite was added. Heating was continued with stirring for 2 hours, after which the mixture was cooled to room temperature. The resulting solid was collected by filtration and washed with water until the filtrate was neutral. The solid was dried at 80° C. to give 26.2 g (75% yield) of 1-amino-4-hydroxyanthraquinone. 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 resulting 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-e7ee6218e44545c0b9c81a978beb3f0b
Source dataset
uspto-grants-1978_08
Patent number
US04105680

Linked notes

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