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

HRID 1579672Notes

Reaction equation

HRID 1579672 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]>C(C(C)=O)C.O.O.O.O.[Fe](Cl)Cl>[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

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 178516261HCID 178516261, compound

Product 1

HCID 123364025-Nitronaphthalene-1,4-dione

Reagents, catalysts & solvents 2

HCID 16211588Ferrous chloride tetrahydrateCatalystHCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
50 °C

Procedure

5.5 g (0.025 mol) of 8-nitro-1,4-naphthoquinone-1-oxime and 21 g (0.11 mol) of iron (II) chloride tetrahydrate are heated to reflux temperature in 100 ml of methyl ethyl ketone. 25 g of hydrogen chloride gas are then introduced over a period of 20 minutes during which the sump temperature is kept at 87° to 90°C. The reaction mixture is stirred for another hour at this temperature, after which it is poured into 1000 ml of water heated to approximately 50°C, followed by stirring for 30 minutes at that temperature. The reaction product precipitated is then filtered off under suction. Recrystallization from toluene following the addition of 2 g of active carbon gives 4 g (78 percent of the theoretical yield) of 5-nitro-1,4-naphthoquinone melting at 164°C.

Workup

  1. customis kept at 87° to 90°C
  2. stirringby stirring for 30 minutes at that temperature
  3. customThe reaction product precipitated
  4. filtrationis then filtered off under suction
  5. customRecrystallization from toluene following
  6. additionthe addition of 2 g of active carbon
  7. customgives 4 g (78 percent of the

Sources & evidence

ORD record
ord-c04dc669b26b444a9d4128976fe220ef
Source dataset
uspto-grants-1976_01
Patent number
US03931255

Reaction notes

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