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

HRID 1579671Notes

Reaction equation

HRID 1579671 reaction equation
Cl.[N+:2]([C:5]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:6]=1[C:7](=[O:17])[CH:8]=[CH:9][C:10]2=NO)([O-:4])=[O:3].[OH2:18]>O.O.O.O.[Fe](Cl)Cl>[N+:2]([C:5]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:6]=1[C:7](=[O:17])[CH:8]=[CH:9][C:10]2=[O:18])([O-:4])=[O:3]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 962WaterHCID 178516262HCID 178516262, compound

Product 1

HCID 123364025-Nitronaphthalene-1,4-dione

Reagents, catalysts & solvents 1

HCID 16211588Ferrous chloride tetrahydrateCatalyst

Conditions

Temperature
40 °C

Procedure

120 ml of 37 percent by weight aqueous hydrochloric acid and 42 g (0.21 mol) of iron (II) chloride tetrahydrate are introduced into a reaction vessel and saturated with approximately 8 g of gaseous hydrogen chloride. 11 g of 5-nitro-1,4-naphthoquinone-1-oxime are introduced at a temperature of about 20° to 25°C. The reaction mixture is kept at the temperature indicated with stirring and, after 2 hours, is poured into 1,000 ml of water heated to approximately 40°C. followed by stirring for 30 minutes. The reaction product precipitated is then filtered off under suction, washed with water until neutral and dried at approximately 50°C. 5-Nitro-1,4-naphthoquinone melting at 161°C is thus obtained in a yield of 9.8 g (96 percent of the theoretical yield).

Workup

  1. stirringby stirring for 30 minutes
  2. customThe reaction product precipitated
  3. filtrationis then filtered off under suction
  4. washwashed with water until neutral and
  5. customdried at approximately 50°C

Sources & evidence

ORD record
ord-d25175768ea34ebf9fb675a920701564
Source dataset
uspto-grants-1976_01
Patent number
US03931255

Reaction notes

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