1-methyl-4-(3-nitro-5-(trifluoromethyl)phenyl)-1H-pyrazole → 3-(1-methyl-1H-pyrazol-4-yl)-5-(trifluoromethyl)aniline

HRID 1050193Notes

Reaction equation

HRID 1050193 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[C:9]([N+:17]([O-])=O)[CH:8]=2)[CH:4]=[N:3]1>CO.[Pd]>[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:8]=[C:9]([CH:10]=[C:11]([C:13]([F:14])([F:15])[F:16])[CH:12]=2)[NH2:17])[CH:4]=[N:3]1

Participants

4

Reactant 1

HCID 904231661-methyl-4-(3-nitro-5-(trifluoromethyl)phenyl)-1H-pyrazole

Product 1

HCID 904234893-(1-methyl-1H-pyrazol-4-yl)-5-(trifluoromethyl)anilineYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a suspension of 1-methyl-4-(3-nitro-5-(trifluoromethyl)phenyl)-1H-pyrazole (300 mg, 1.106 mmol) in MeOH (10 mL) was added Pd/C (118 mg, 1.106 mmol). The mixture was hydrogenated at 40 psi at 28° C. for 12 h under a H2 atmosphere. Then the solution was filtered and concentrated to yield 3-(1-methyl-1H-pyrazol-4-yl)-5-(trifluoromethyl)aniline (240 mg, 0.995 mmol, 90% yield). TLC (PE/EA=1:1, Rf=0.3): 1H NMR (400 MHz, CD3OD) δ 7.98 (s, 1H), 7.81 (s, 1H), 7.16 (d, J=7.3 Hz, 2H), 6.88 (s, 1H), 3.92 (s, 3H). ES-LCMS m/z 242 (M+H).

Workup

  1. filtrationThen the solution was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-d9ac012867e34a249698bb4f6e0032de
Source dataset
uspto-grants-2016_07
Patent number
US09382238B2

Reaction notes

Loading…