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Hydrochloric Acid → 2-Chloro-4-nitroaniline

HRID 364700
Notes
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Reaction equation

HRID 364700 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.ClCl.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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 74302,6-Dichloro-4-nitroanilineHCID 74754-Nitroaniline2×HCID 24526Chlorine

Product 1

HCID 84922-Chloro-4-nitroanilineYield 90%

Reagents, catalysts & solvents 2

HCID 944
Nitric Acid
Solvent
HCID 962WaterSolvent

Procedure

It has now been found that 2,6-dichloro-4-nitroaniline can be prepared in a high purity (purity of at least 96%) and a high yield (90% of theory) without the deficiencies mentioned, such as pollution of the effluent and technical effort for regeneration and working up of the effluent, by chlorination of 4-nitroaniline in water with chlorine bleaching liquor, by chlorinating 1 mole of 4-nitroaniline in 3-6 moles 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°-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 preferably with renewed addition of dispersing agent, and then by afterchlorinating, by renewed addition of chlorine bleaching liquor, at temperatures between 20° and 70° C., subsequently bringing the pH of the aqueous suspension to 9.0 and filtering off the 2,6-dichloro-4-nitroaniline formed and washing it with dilute mineral acid.

Workup

  1. customcan be prepared in a high purity (purity of at least 96%)
  2. customa high yield (90% of theory) without the deficiencies
  3. customis stable under the reaction conditions
  4. custominitially being carried out at 5°-10° C.

Sources & evidence

ORD record
ord-c24e918046504812b1906301e4008f20
Source dataset
uspto-grants-1986_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04605767

Reaction notes

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