Ammonia → 4-Nitro-3-(trifluoromethyl)aniline

HRID 1199538Notes

Reaction equation

HRID 1199538 reaction equation
[NH3:1].[F:2][C:3]([F:15])([F:14])[C:4]1[CH:5]=[C:6](F)[CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11]>O>[N+:10]([C:9]1[CH:8]=[CH:7][C:6]([NH2:1])=[CH:5][C:4]=1[C:3]([F:15])([F:14])[F:2])([O-:12])=[O:11]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 2230945-Fluoro-2-nitrobenzotrifluoride

Product 1

HCID 949554-Nitro-3-(trifluoromethyl)aniline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of ammonia in water (100 cm3, s.g. 0.88) was added to 3-trifluoromethyl-4-nitrofluorobenzene (5 g) and the mixture was heated in a bomb at 150° for 2 hours. Solvent was removed in vacuo to yield a yellow solid. Recrystallization of this solid from hexane/ethyl acetate afforded yellow crystals of 4-nitro-3-trifluoromethylaniline, m.p. 134°, (3.5 g).

Workup

  1. temperaturethe mixture was heated in a bomb at 150° for 2 hours
  2. customSolvent was removed in vacuo
  3. customto yield a yellow solid
  4. customRecrystallization of this solid from hexane/ethyl acetate afforded yellow crystals of 4-nitro-3-trifluoromethylaniline, m.p. 134°, (3.5 g)

Sources & evidence

ORD record
ord-2fcae59dac3447b6aae600a778d82adc
Source dataset
uspto-grants-1990_02
Patent number
US04900839

Reaction notes

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