Nitric Acid → 1,4-Dichloro-6-nitroanthracene-9,10-dione

HRID 647250Notes

Reaction equation

HRID 647250 reaction equation
[N+:1]([O-:4])(O)=[O:2].[Cl:5][C:6]1[C:19]2[C:18](=[O:20])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11](=[O:21])[C:10]=2[C:9]([Cl:22])=[CH:8][CH:7]=1.OS(O)(=O)=O>>[Cl:5][C:6]1[C:19]2[C:18](=[O:20])[C:17]3[C:12](=[CH:13][C:14]([N+:1]([O-:4])=[O:2])=[CH:15][CH:16]=3)[C:11](=[O:21])[C:10]=2[C:9]([Cl:22])=[CH:8][CH:7]=1

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 41794241,4-Dichloroanthraquinone

Product 1

HCID 204859721,4-Dichloro-6-nitroanthracene-9,10-dione

Procedure

80 g of a mixed acid containing 33% of HNO3 are added dropwise at 5° to 10° C. in the course of 2 to 4 hours to a solution of 110.0 g of 1,4-dichloroanthraquinone in 600 ml of 96% strength H2SO4. The mixture is allowed slowly to warm to room temperature, and is then stirred for a further few hours, and the precipitated 1,4-dichloro-5-nitroanthraquinone (112.6 g) is filtered off with suction. The mother liquor is stirred into 2 liters of water. The solids are then filtered off with suction, and the press cake is washed with water until neutral and dried at 100° C. 12.7 g of 1,4-dichloro-6-nitroanthraquinone are isolated.

Workup

  1. filtrationthe precipitated 1,4-dichloro-5-nitroanthraquinone (112.6 g) is filtered off with suction
  2. stirringThe mother liquor is stirred into 2 liters of water
  3. filtrationThe solids are then filtered off with suction
  4. washthe press cake is washed with water until neutral and
  5. customdried at 100° C

Sources & evidence

ORD record
ord-46c472452a7a4e18847fa7ee3ab9eedf
Source dataset
uspto-grants-1983_10
Patent number
US04408056

Reaction notes

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