1-Chloro-4-nitrobenzene → 4-Nitrodiphenylamine

HRID 903521Notes

Reaction equation

HRID 903521 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7](Cl)=[CH:6][CH:5]=1)([O-:3])=[O:2].C([NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=O.C(=O)([O-])[O-].[K+].[K+].[OH-].[Na+]>O.C1(C)C(C)=CC=CC=1>[CH:17]1[CH:18]=[CH:19][C:14]([NH:13][C:7]2[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)=[CH:15][CH:16]=1

Participants

7

Reactant 4

HCID 74741-Chloro-4-nitrobenzeneHCID 7671FormanilideHCID 11430Potassium CarbonateHCID 14798Sodium Hydroxide

Product 1

HCID 132714-Nitrodiphenylamine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7237O-XyleneSolvent

Conditions

Temperature
205 °C

Procedure

To a charge of 157 grams of p-nitrochlorobenzene (1 mole), 169 grams of formanilide (1.4 moles) and 50 grams of xylene at 180° C. is fed over a period of about 4 hours a solution of 58 grams of potassium carbonate (0.42 mole) and 22.5 grams of sodium hydroxide (0.56 mole) in 120 grams of water. Water is removed concurrently from the reaction mixture with the addition of the aforesaid solution. The temperature of the reaction mixture is then raised to 205° C. and heated at such temperature for 11/2 hours. The amounts of 4-nitrodiphenylamine formed and p-nitrochlorobenzene remaining unreacted are then determined, as described in Example 1. The yield of 4-nitrodiphenylamine is 69.3%, and the conversion of the p-nitrochlorobenzene charged is 78.4 or 88.4%.

Workup

  1. customWater is removed concurrently from the reaction mixture with the addition of the aforesaid solution
  2. temperatureheated at such temperature for 11/2 hours

Sources & evidence

ORD record
ord-2273192416df4d3b84662e11fca288c9
Source dataset
uspto-grants-1980_10
Patent number
US04228103

Reaction notes

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