4-Chloro-3,5-dinitrobenzotrifluoride → 2,6-Dinitro-4-(trifluoromethyl)aniline

HRID 1112381Notes

Reaction equation

HRID 1112381 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[C:6]([N+:14]([O-:16])=[O:15])[C:5]=1Cl)([O-:3])=[O:2].[OH-].[NH4+:19]>C1C=CC=CC=1>[N+:1]([C:4]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[C:6]([N+:14]([O-:16])=[O:15])[C:5]=1[NH2:19])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 98094-Chloro-3,5-dinitrobenzotrifluorideHCID 14923Ammonium Hydroxide2×

Product 1

HCID 99362,6-Dinitro-4-(trifluoromethyl)aniline

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 40.5 g. of 2,6-dinitro-4-trifluoromethyl-1-chlorobenzene in 300 ml. of benzene was mixed with 250 ml. of 14 N ammonium hydroxide. The reaction mixture was stirred at room temperature for about 1.5 hours, at which point in time another 100 ml. of 14 N ammonium hydroxide were added and the stirring was continued for an additional 2 hours. The organic layer was separated, was washed with water and was dried. Removal of the solvents in vacuo yielded 2,6-dinitro-4-trifluoromethylaniline, which melted at about 142°-144° C. after recrystallization from a hexane-benzene solvent mixture.

Workup

  1. waitthe stirring was continued for an additional 2 hours
  2. customThe organic layer was separated
  3. washwas washed with water
  4. customwas dried
  5. customRemoval of the solvents in vacuo

Sources & evidence

ORD record
ord-0944b39f8647472ca008706ce5574c70
Source dataset
uspto-grants-1978_10
Patent number
US04122184

Reaction notes

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