5-Nitro-2-(4-(trifluoromethyl)phenyl)pyridine → 6-(4-(Trifluoromethyl)phenyl)pyridin-3-amine

HRID 2173806Notes

Reaction equation

HRID 2173806 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)=[N:8][CH:9]=1)([O-])=O.[H][H]>C(O)C.O1CCCC1.[Pd]>[F:19][C:16]([F:17])([F:18])[C:13]1[CH:12]=[CH:11][C:10]([C:7]2[N:8]=[CH:9][C:4]([NH2:1])=[CH:5][CH:6]=2)=[CH:15][CH:14]=1

Participants

6

Reactant 2

HCID 679808515-Nitro-2-(4-(trifluoromethyl)phenyl)pyridineHCID 178418361HCID 178418361, compound

Product 1

HCID 596413736-(4-(Trifluoromethyl)phenyl)pyridin-3-amineYield 95.2%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-nitro-2-(4-(trifluoromethyl)phenyl)pyridine (260 mg, 0.97 mmol) in ethanol (10 mL) and tetrahydrofuran (5 mL) was added 10 wt % palladium on carbon (100 mg). The reaction was pressurized to 50 psi hydrogen and stirred at room temperature for 4 hours. The reaction was filtered through Celite and concentrated to give 6-(4-(trifluoromethyl)phenyl)pyridin-3-amine (220 mg, 95%). 1H NMR (400 MHz, CD3OD, δ): 7.98 (s, 1H), 7.88 (d, 2H), 7.60 (d2, H), 7.54 (d, 1H), 7.09 (d, 1H).

Workup

  1. filtrationThe reaction was filtered through Celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-4fe3e4b817b04fb0b35903aaf0648dea
Source dataset
uspto-grants-2015_06
Patent number
US09056834B2

Reaction notes

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