Ammonia → 1-Aminoanthraquinone

HRID 616858Notes

Reaction equation

HRID 616858 reaction equation
[N+:1]([C:4]1[C:17]2[C:16](=[O:18])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9](=[O:19])[C:8]=2[CH:7]=[CH:6][CH:5]=1)([O-])=O.[NH4+].[Cl-].N>O>[NH2:1][C:4]1[C:17]2[C:16](=[O:18])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9](=[O:19])[C:8]=2[CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 67041-NitroanthraquinoneHCID 25517Ammonium Chloride

Product 1

HCID 67101-AminoanthraquinoneYield 100.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

75 g of 1-nitroanthraquinone (98.5 % strength) are heated to 180° C in 145 ml of water. Thereafter, a cold solution of 14.6 g of NH4Cl in 240 ml of 25 % strength aqueous ammonia is pumped into this mixture within 5 minutes. The temperature is kept constant for 1 hour, the pressure rising during this period to 51 bar. After cooling and releasing pressure, the product is filtered off by suction and washed with water. Both filtrate and washing water (1 liter) are slightly yellow in color, E47010 cm = 13.0. 66.7 g of 95.2 % pure 1-aminoanthraquinone (97.5 % of theory) are obtained. The product still contains about 1.0% of 1-nitroanthraquinone.

Workup

  1. waitthe pressure rising during this period to 51 bar
  2. temperatureAfter cooling
  3. filtrationthe product is filtered off by suction
  4. washwashed with water
  5. washBoth filtrate and washing water (1 liter)

Sources & evidence

ORD record
ord-ee2685725bfc48449a2efd952692231b
Source dataset
uspto-grants-1978_02
Patent number
US04076736

Reaction notes

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