Nitrogen → 2-(1H-pyrazol-1-yl)-5-(trifluoromethyl)aniline

HRID 643858Notes

Reaction equation

HRID 643858 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:6][C:5]=1[N:14]1[CH:18]=[CH:17][CH:16]=[N:15]1)([O-])=O.N#N>CCO.[Pd]>[N:14]1([C:5]2[CH:6]=[CH:7][C:8]([C:10]([F:12])([F:13])[F:11])=[CH:9][C:4]=2[NH2:1])[CH:18]=[CH:17][CH:16]=[N:15]1

Participants

5

Reactant 2

HCID 947NitrogenHCID 55238268HCID 55238268, compound

Product 1

HCID 70640332-(1H-pyrazol-1-yl)-5-(trifluoromethyl)anilineYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Compound 73 (206 mg, 0.8 mmol) was dissolved in EtOH (25 mL) in a 50 mL flask. 2 spatulas of 5% Pd on Activated Carbon and a stirrbar was added followed by evacuation and N2(g) purging of the flask. H2(g) was then introduced into the flask by a balloon and the reaction stirred at room temperature under H2-atmosphere for 2 h. The H2(g) inlet was closed and the flask evacuated and N2(g) purged 3 times. LC/MS analysis showed complete hydrogenation and the mixture was filtered through a plug of Celite before removal of the solvent in vacuo to afford the crude aniline (163 mg, 90%). LC/MS, >95%, m/z (ESI+)=228 (MH+).

Workup

  1. custompurging of the flask
  2. additionH2(g) was then introduced into the flask by a balloon
  3. customThe H2(g) inlet was closed
  4. customthe flask evacuated
  5. customN2(g) purged 3 times
  6. filtrationthe mixture was filtered through a plug of Celite before removal of the solvent in vacuo

Sources & evidence

ORD record
ord-316d63321c3b445799c37e17e282186c
Source dataset
uspto-grants-2010_04
Patent number
US07700552B2

Reaction notes

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