Hydrochloric Acid → 3,5-Dichloroaniline

HRID 1462648Notes

Reaction equation

HRID 1462648 reaction equation
ClC1C(Cl)=C(C=CC=1)N(Cl)Cl.Cl[C:13]1[C:18]([NH2:19])=[C:17](Cl)[C:16]([Cl:21])=[C:15](Cl)[C:14]=1[Cl:23].C1(C)C(O)=CC=CC=1.Cl.[H][H].[OH-].[Na+]>[Pd].C.[Ta].O.C1(C)C=CC=CC=1>[Cl:21][C:16]1[CH:17]=[C:18]([CH:13]=[C:14]([Cl:23])[CH:15]=1)[NH2:19]

Participants

10

Reactant 5

HCID 313Hydrochloric AcidHCID 335O-CresolHCID 14798Sodium HydroxideHCID 131713377HCID 131713377, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 122813,5-Dichloroaniline

Reagents, catalysts & solvents 4

HCID 23956TantalumCatalystHCID 14818447PalladiumcarbonCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

131 parts of a tetrachloroaniline/pentachloroaniline isomer mixture (according to Example 2), 200 parts of o-cresol and 20 parts of a Pd/charcoal catalyst (1% strength) and 5 parts of concentrated hydrochloric acid are reacted with hydrogen at 175° C. and under 50 bar in a tantalum autoclave, in the course of 10 hours. After the autoclave has been cooled and the pressure released, the mixture is rendered alkaline with 200 parts of toluene, 400 parts of water and 250 parts of aqueous concentrated sodium hydroxide solution, and is heated to the boil, and thereafter the catalyst is separated off by filtering under suction. After extracting the aqueous alkaline phase by shaking with toluene, the toluene solutions of 3,5-dichloroaniline are distilled. 85 parts of a 98% strength 3,5-dichloroaniline, bp. 130°-136°/18 mbar, are obtained.

Workup

  1. temperatureAfter the autoclave has been cooled
  2. temperatureis heated to the boil
  3. customthe catalyst is separated off
  4. filtrationby filtering under suction
  5. extractionAfter extracting the aqueous alkaline phase
  6. distillationthe toluene solutions of 3,5-dichloroaniline are distilled

Sources & evidence

ORD record
ord-b070175815444e8b908c6f5f0f8edd78
Source dataset
uspto-grants-1984_07
Patent number
US04460788

Reaction notes

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