3-(Trifluoromethyl)aniline → HCID 19978912, compound

HRID 1461632Notes

Reaction equation

HRID 1461632 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:6][CH:7]=1.[F:12][C:13]1[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=1[CH:15]=O>C1(C)C=CC=CC=1>[F:12][C:13]1[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=1[CH:15]=[N:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([F:9])([F:10])[F:11])[CH:3]=1

Participants

4

Reactant 2

HCID 73753-(Trifluoromethyl)anilineHCID 67970o-Fluorobenzaldehyde

Product 1

HCID 19978912HCID 19978912, compoundYield 104.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a toluene (200 mL) solution of 3-aminobenzotrifluoride (10.4 grams, 0.06 mol) was added 2-fluorobenzaldehyde (8.0 grams, 0.06 mol). The mixture was heated under reflux with a Dean-Stark trap for 6 hours. The solvent was removed in a rotary evaporator to give 2-fluorobenzylidene 3-trifluoromethylaniline (16.8 grams, 97% yield, yellow liquid) whose structure was confirmed by nuclear magnetic resonance, infra-red spectroscopy, and mass spectroscopy analysis.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux with a Dean-Stark trap for 6 hours
  3. customThe solvent was removed in a rotary evaporator

Sources & evidence

ORD record
ord-5570d17b91f744f8b364457c7e45387a
Source dataset
uspto-grants-1991_12
Patent number
US05076832

Reaction notes

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