Aniline → 4-Nitrodiphenylamine

HRID 1669990Notes

Reaction equation

HRID 1669990 reaction equation
C(NC1C=CC=CC=1)=O.[NH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[N+:17]([C:20]1[CH:25]=[CH:24][C:23](Cl)=[CH:22][CH:21]=1)([O-:19])=[O:18].C(=O)([O-])[O-].[K+].[K+]>C(O)=O>[CH:14]1[CH:15]=[CH:16][C:11]([NH:10][C:23]2[CH:24]=[CH:25][C:20]([N+:17]([O-:19])=[O:18])=[CH:21][CH:22]=2)=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 6115AnilineHCID 74741-Chloro-4-nitrobenzeneHCID 7671Formanilide2×HCID 11430Potassium Carbonate

Product 1

HCID 132714-Nitrodiphenylamine

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

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-b03605c78dcf4e78a4a10ac06410f8e1
Source dataset
uspto-grants-2011_08
Patent number
US07989662B2

Reaction notes

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