Hydrochloric Acid → 5-Nitronaphthalene-1,4-dione

HRID 1579673Notes

Reaction equation

HRID 1579673 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[C:12](=NO)[CH:11]=[CH:10][C:9]2=[O:16])([O-:3])=[O:2].Cl.[OH2:18]>O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Fe+2]>[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[C:12](=[O:18])[CH:11]=[CH:10][C:9]2=[O:16])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 178516261HCID 178516261, compound

Product 1

HCID 123364025-Nitronaphthalene-1,4-dione

Reagents, catalysts & solvents 1

HCID 62662Ferrous sulfate heptahydrateCatalyst

Conditions

Temperature
33 °C

Procedure

5.5 g of 8-nitro-1,4-naphthoquinone-1-oxime are suspended in 450 ml of 38 percent by weight aqueous hydrochloric acid, followed by heating to 33°C. 61 g (0.22 mol) of iron (II) sulphate heptahydrate are then introduced in portions with stirring. After 1.5 hours, the reaction mixture is poured into 1000 ml of water heated to approximately 50°C, followed by stirring for 1 hour at that temperature. The reaction product precipitated is filtered off under suction, washed with water until neutral and dried at approximately 50°C. The yield amounts to 4 g (78 percent of the theoretical yield) of 5-nitro-1,4-naphthoquinone melting at 160°C.

Workup

  1. temperatureheated to approximately 50°C
  2. stirringby stirring for 1 hour at that temperature
  3. customThe reaction product precipitated
  4. filtrationis filtered off under suction
  5. washwashed with water until neutral and
  6. customdried at approximately 50°C

Sources & evidence

ORD record
ord-fe0745702522414abe7541d1a80a01d6
Source dataset
uspto-grants-1976_01
Patent number
US03931255

Reaction notes

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