Benzene, 4-nitro-1-(2-propen-1-yl)-2-(trifluoromethyl)- → 4-Propyl-3-(trifluoromethyl)aniline

HRID 1773238

Reaction equation

HRID 1773238 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-])=O)=[CH:6][C:5]=1[C:13]([F:16])([F:15])[F:14])[CH:2]=[CH2:3]>C1COCC1.O.[Pd]>[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[CH:6][C:5]=1[C:13]([F:14])([F:15])[F:16])[CH2:2][CH3:3]

Participants

5

Reactant 1

HCID 9816036Benzene, 4-nitro-1-(2-propen-1-yl)-2-(trifluoromethyl)-

Product 1

HCID 215337204-Propyl-3-(trifluoromethyl)anilineYield 66.8%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-allyl-4-nitro-2-(trifluoromethyl)benzene (750 mg, 3.24 mmol) in 18 mL of THF and 3.6 mL of H2O was added 10% Pd/C (250 mg, 3.24 mmol). The reaction was stirred at room temperature under an H2 balloon for 24 hr. After filtering to remove Pd/C, the reaction solution was concentrated under reduced pressure. The residue was purified by silica gel flash chromatography, 100% Heptane-10% Ethyl Acetate/90% Heptane, to give 4-propyl-3-(trifluoromethyl)aniline (440 mg). LCMS retention time=1.53 minutes (LC method 3); MS (m+1)=203.8. 1H NMR (400 MHz, DMSO-d6) δ 0.93 (t, J=7.4 Hz, 3H), 1.54 (sxt, J=7.6 Hz, 2H), 2.51-2.56 (m, 2H), 5.66 (s, 2H), 6.44 (dd, J=8.5, 1.9 Hz, 1H), 6.52 (d, J=2.1 Hz, 1H), 7.24 (d, J=8.6 Hz, 1H).

Workup

  1. filtrationAfter filtering
  2. customto remove Pd/C
  3. concentrationthe reaction solution was concentrated under reduced pressure
  4. customThe residue was purified by silica gel flash chromatography, 100% Heptane-10% Ethyl Acetate/90% Heptane

Sources & evidence

ORD record
ord-40d74fdf2d2844abb991a9143709ec60
Source dataset
uspto-grants-2016_02
Patent number
US09255093B2

Linked notes

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