1-Nitroanthraquinone → 1-Aminoanthraquinone

HRID 328147Notes

Reaction equation

HRID 328147 reaction equation
O.NN.[OH-].[Na+].[N+:6]([C:9]1[C:22]2[C:21](=[O:23])[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14](=[O:24])[C:13]=2[CH:12]=[CH:11][CH:10]=1)([O-])=O>O>[NH2:6][C:9]1[C:22]2[C:21](=[O:23])[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14](=[O:24])[C:13]=2[CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 67041-Nitroanthraquinone2×HCID 14798Sodium Hydroxide2×HCID 24654Hydrazine hydrate (1:1)

Product 1

HCID 67101-Aminoanthraquinone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

500 Parts of water, 20 parts of hydrazine hydrate and 100 parts of 30% sodium hydroxide solution are heated to 70°. 51 Parts of 1-nitro-anthraquinone are entered over the course of 1 hour. The temperature of the reaction mixture is kept at between 70° and 75°. After the addition of the whole amount of 1-nitroanthraquinone, the suspension is heated to 80° and stirred for 1 hour. 70 Parts of 40% sodium hydroxide solution are subsequently added. The reaction mass is then stirred at 90° over the course of 90 minutes and filtered. The precipitate is washed with water until the filtrate is colourless and neutral, and then dried. 43 Parts of 1-amino-anthraquinone are obtained.

Workup

  1. customare entered over the course of 1 hour
  2. customis kept at between 70° and 75°
  3. temperaturethe suspension is heated to 80°
  4. stirringThe reaction mass is then stirred at 90° over the course of 90 minutes
  5. filtrationfiltered
  6. washThe precipitate is washed with water until the filtrate
  7. customneutral, and then dried

Sources & evidence

ORD record
ord-fc95999e0d6c4f24bc099d08ed643957
Source dataset
uspto-grants-1977_04
Patent number
US04016182

Reaction notes

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