5-Nitro-4-amino-1-naphthol → 5-Nitronaphthalene-1,4-dione

HRID 1579669Notes

Reaction equation

HRID 1579669 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].[N+](C1C=CC=C2C=1C(=O)C=CC2=NO)([O-])=[O:18].[N+](C1C=CC=C2C=1C(N)=CC=C2O)([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 215690055-Nitro-4-amino-1-naphtholHCID 178516261HCID 178516261, compoundHCID 178516262HCID 178516262, compound

Product 1

HCID 123364025-Nitronaphthalene-1,4-dione

Reagents, catalysts & solvents 1

HCID 27284Ferrous cationCatalyst

Procedure

5-Nitro-1,4-naphthoquinone is prepared by reducing 8-nitro-1,4-naphthoquinone-1-oxime and/or 5-nitro-1,4-naphthoquinone-1-oxime in an aqueous and/or organic reaction medium in the presence of iron (II) ions and a hydrogen halide at a temperature in the range of from -20° to 100°C, and thereafter oxidizing the 8- and and/or 5-nitro-4-amino-1-naphthol formed, or the corresponding salt, optionally without intermediate isolation, at a temperature in the range of from -10° to 100°C to form the desired 5-nitro-1,4-naphthoquinone.

Workup

  1. custom5-Nitro-1,4-naphthoquinone is prepared
  2. customof from -20° to 100°C
  3. customformed

Sources & evidence

ORD record
ord-0086968c91504490ba5b4f7d4f16714a
Source dataset
uspto-grants-1976_01
Patent number
US03931255

Reaction notes

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