4-Nitrodiphenylamine → N-Phenyl-p-phenylenediamine

HRID 2360956Notes

Reaction equation

[CH:1]1[CH:6]=[CH:5][C:4]([NH:7][C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][CH:9]=2)=[CH:3][CH:2]=1.[S-2].[Na+].[Na+]>>[CH:1]1[CH:2]=[CH:3][C:4]([NH:7][C:8]2[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=2)=[CH:5][CH:6]=1

Participants

Reactant 2

HCID 132714-Nitrodiphenylamine

HCID 14804Sodium Sulfide

Product 1

HCID 7564N-Phenyl-p-phenylenediamine

Procedure

formanilide method, where formic acid and aniline are used as starting materials to prepare formanilide, which in turn reacts with p-nitro-chlorobenzene in the presence of an acid-binding agent such as potassium carbonate, to produce 4-nitrodiphenylamine, and then, 4-nitrodiphenylamine is reduced by sodium sulfide to form 4-aminodiphenylamine;

Sources & evidence

ORD record: ord-8bcfd77001f349b3a7943aa74440a071
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08686188B2

Reaction notes

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