9,10-Anthracenedione, 1,5-dinitro- → HCID 20474966, compound

HRID 2295303Notes

Reaction equation

HRID 2295303 reaction equation
[N+:1]([C:4]1[C:17]2[C:16](=[O:18])[C:15]3[C:10](=[C:11]([N+:19]([O-])=O)[CH:12]=[CH:13][CH:14]=3)[C:9](=[O:22])[C:8]=2[CH:7]=[CH:6][CH:5]=1)([O-:3])=[O:2].[OH:23]S(O)(=O)=O.O=S(=O)=O.B(O)(O)O>S(=O)(=O)(O)O.O>[OH:23][C:14]1[C:15]2[C:16](=[O:18])[C:17]3[C:8](=[CH:7][CH:6]=[CH:5][C:4]=3[N+:1]([O-:3])=[O:2])[C:9](=[O:22])[C:10]=2[C:11]([NH2:19])=[CH:12][CH:13]=1

Participants

6

Reactant 3

HCID 67059,10-Anthracenedione, 1,5-dinitro-HCID 7628Boric AcidHCID 24681Fuming sulfuric acid

Product 1

HCID 20474966HCID 20474966, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Procedure

30 parts of 1,5-dinitroanthraquinone are stirred in 300 parts of 28% strength oleum for 4 hours at 50° to 60° C. 15 parts of boric acid are then added with cooling and dissolved. The reaction mixture is then diluted with 57.5 parts of 78% sulphuric acid and 156 parts of water, while cooling is continued, and stirred for 15 hours at room temperature. The reaction mixture is discharged onto 2,000 parts of ice, and the product is filtered off with suction and washed with warm water until neutral. After the product has been stirred with 500 parts of a 10% strength aqueous pyridine solution at 90° to 100° C., filtered off with suction and washed, 16 parts of 1-hydroxy-4-amino-8-nitroanthraquinone are obtained.

Workup

  1. temperaturewith cooling
  2. dissolutiondissolved
  3. temperaturewhile cooling
  4. filtrationthe product is filtered off with suction
  5. washwashed with warm water until neutral
  6. stirringAfter the product has been stirred with 500 parts of a 10% strength aqueous pyridine solution at 90° to 100° C.
  7. filtrationfiltered off with suction
  8. washwashed

Sources & evidence

ORD record
ord-e6d6f85c39564f4798abe981d56e989d
Source dataset
uspto-grants-1984_01
Patent number
US04424160

Reaction notes

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