Hydrochloric Acid → HCID 22447523, compound

HRID 2188257Notes

Reaction equation

HRID 2188257 reaction equation
[Cl:1][C:2]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=[CH:5][C:3]=1[NH2:4].ClC1C=CC(C(F)(F)F)=CC=1N.Cl>[Ni].C(O)C.ClC1C=CC=CC=1>[ClH:1].[Cl:1][C:2]1[CH:8]=[C:7]([C:9]([F:10])([F:11])[F:12])[CH:6]=[CH:5][C:3]=1[NH2:4]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 8475Benzenamine, 2-chloro-5-(trifluoromethyl)-HCID 1620012-Chloro-4-trifluoromethylaniline

Product 1

HCID 22447523HCID 22447523, compound

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 702EthanolSolvent2×HCID 7964ChlorobenzeneSolvent

Procedure

Raney Nickel (0.7 g) was added to a solution of the above isomer mixture (35.85 g) in ethanol in a hydrogenation reactor at 50° C. under hydrogen at 5 bar for 5 hours. The mixture was cooled, filtered and evaporated to give a 95/5 mixture of 2-chloro-4-trifluoromethylaniline and 2-chloro-5-trifluoromethylaniline (33.1 g). Hydrogen chloride gas was added over 0.5 hour to a solution of the above mixture in ethanol and chlorobenzene, cooled to 0° C., and filtered to give 2-chloro-4-trifluoromethylaniline hydrochloride (33.5 g), having a purity of >99%. The overall yield from 3,4-dichlorobenzotrifluoride was 85%.

Workup

  1. temperatureThe mixture was cooled
  2. filtrationfiltered
  3. customevaporated
  4. customto give
  5. filtrationfiltered

Sources & evidence

ORD record
ord-45b647753de0468092d9ae279b81c5c7
Source dataset
uspto-grants-2002_06
Patent number
US06410737B1

Reaction notes

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