1-Nitroanthraquinone → 1-Aminoanthraquinone

HRID 2057874Notes

Reaction equation

HRID 2057874 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>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

3

Reactant 1

HCID 67041-Nitroanthraquinone

Product 1

HCID 67101-Aminoanthraquinone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

750 ml of water and 324 g of Na2S.9H2O are heated to 90°-95° C. in a cylindrical reaction vessel (1.5 l capacity, diameter 10 cm, height 20 cm) with a lid fitted with three tubes, which is provided with an anchor stirrer (diameter 9 cm, anchor height 12 cm) and thermometer, 81 g of finely sieved 1-nitro-anthraquinone (content 73.9%) is then stirred in at the same temperature in the course of one hour and finally the mixture is subsequently stirred at 90°-95° C. for 30 minutes. The reaction mixture is filtered and the residue is washed with hot water until neutral and dried at 60° C. in vacuo. 71.3 g of crude 1-amino-anthraquinone of the following composition are obtained: 72.5% of 1-amino-anthraquinone=98% of theory, 3.1% of 1,5-diamino-anthraquinone, 2.8% of 1,8-diamino-anthraquinone, 3.0% of 1,6-diamino-anthraquinone, 3.1 % of 1,7-diaminoanthraquinone, 2.3% of anthraquinone, 5.9% of 2-amino-anthraquinone and 0.1% of 2,6-+2,7-diamino-anthraquinone.

Workup

  1. customfitted with three tubes
  2. customwhich is provided with an anchor stirrer (diameter 9 cm, anchor height 12 cm)
  3. filtrationThe reaction mixture is filtered
  4. washthe residue is washed with hot water until neutral and
  5. customdried at 60° C. in vacuo

Sources & evidence

ORD record
ord-3a59363ea4b84272b94ae478a07954b5
Source dataset
uspto-grants-1980_07
Patent number
US04213909

Reaction notes

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