Hydrochloric Acid → 2-Chloro-4-nitroaniline

HRID 364702Notes

Reaction equation

HRID 364702 reaction equation
[Cl:1][C:2]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[C:5](Cl)[C:3]=1[NH2:4].[N+](C1C=CC(N)=CC=1)([O-])=O.Cl>O.[N+]([O-])(O)=O>[Cl:1][C:2]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:3]=1[NH2:4]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 74302,6-Dichloro-4-nitroanilineHCID 74754-Nitroaniline2×

Product 1

HCID 84922-Chloro-4-nitroanilineYield 90%

Reagents, catalysts & solvents 2

HCID 944Nitric AcidSolventHCID 962WaterSolvent

Procedure

A process for the preparation of substantially pure 2,6-dichloro-4nitroaniline by chlorinatin of 4-nitroaniline with chloring bleaching liquor in water using acids, which comprises chlorinating 1 mole of 4-nitroaniline in 3-6 mole of hydrochloric acid (HCl) or nitric acid (HNO3) in the form of a dilute, aqueous acid in the presence of a dispersing agent which is stable under the reaction conditions, the chlorination initially being carried out at 5° to 10° C. and then at 15°-20° C. and, finally, after 90-95% of the 2-chloro-4-nitroaniline intermediately formed has been converted into 2,6-dichloro-4-nitroaniline, the temperature of the aqueous suspension being increased from 15°-20° C. to 70° C., without further addition of chlorine bleaching liquor, and then by post-chlorinating, by renewed addition of chlorine bleaching liquor, at temperatures between 20 ° and 70° C., bringing the pH of the aqueous sispension to 9.0 and filtering off the 2,6-dichloro-4-nitroaniline formed and washing it with dilute mineral acid to provide 2,6-dichloro-4-nitroaniline of a purity of 96% or above, and a melting point of 187°-191° C. and in a yield of 80% or above.

Workup

  1. customis stable under the reaction conditions
  2. custominitially being carried out at 5° to 10° C.

Sources & evidence

ORD record
ord-e0510ca9b65847629230734656dc1e40
Source dataset
uspto-grants-1986_08
Patent number
US04605767

Reaction notes

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