1-Chloro-4-nitrobenzene → 4-Nitrodiphenylamine

HRID 2231415Notes

Reaction equation

[CH:1]([NH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=O.[N+:10]([C:13]1[CH:18]=[CH:17][C:16](Cl)=[CH:15][CH:14]=1)([O-:12])=[O:11].C(=O)([O-])[O-].[K+].[K+].[Al]>>[CH:7]1[CH:8]=[CH:9][C:4]([NH:3][C:16]2[CH:17]=[CH:18][C:13]([N+:10]([O-:12])=[O:11])=[CH:14][CH:15]=2)=[CH:5][CH:6]=1.[CH:13]1[CH:18]=[CH:17][C:1]([N:3]([C:16]2[CH:17]=[CH:18][C:13]([N+:10]([O-:12])=[O:11])=[CH:14][CH:15]=2)[C:4]2[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][CH:5]=2)=[CH:15][CH:14]=1

Participants

Reactant 4

HCID 74741-Chloro-4-nitrobenzene

HCID 7671Formanilide

HCID 11430Potassium Carbonate

HCID 5359268Aluminum

Product 2

HCID 132714-NitrodiphenylamineYield 90%

HCID 51045864,4'-Dinitrotriphenylamine

Conditions

Temperature: 195 °C

Procedure

0.83 mol of formanilide, 0.50 mol of p-nitrochlorobenzene, 0.34 mol of potassium carbonate and 0.20 mol of aluminium granules were introduced into a reaction vessel and heated to 195° C. and the mixture was stirred at this temperature for 135 minutes. Volatile constituents were distilled off with steam and the residue was washed with a little sodium hydroxide solution and water. 0.45 mol (90% of theory) of 4-nitrodiphenylamine and 0.02 mol of 4,4'-dinitrotriphenylamine were obtained.

Workup

distillationVolatile constituents were distilled off with steam
washthe residue was washed with a little sodium hydroxide solution and water

Sources & evidence

ORD record: ord-1168e218c6a24610a5277d4f16f81b87
Source dataset: uspto-grants-1988_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04782185

Reaction notes

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