5-(2-Chloro-5-(trifluoromethyl)phenoxy)-2-nitropyridine → 5-(2-Chloro-5-(trifluoromethyl)phenoxy)pyridin-2-amine

HRID 1036072Notes

Reaction equation

HRID 1036072 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([N+:11]([O-])=O)=[N:9][CH:10]=1>C(O)C.ClCCl.[Pd]>[Cl:1][C:2]1[CH:17]=[CH:16][C:15]([C:18]([F:19])([F:21])[F:20])=[CH:14][C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([NH2:11])=[N:9][CH:10]=1

Participants

4

Reactant 1

HCID 671268785-(2-Chloro-5-(trifluoromethyl)phenoxy)-2-nitropyridine

Product 1

HCID 671269145-(2-Chloro-5-(trifluoromethyl)phenoxy)pyridin-2-amineYield 96.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584144Dichloromethane ethanolSolvent

Procedure

10% Pd/C (38 mg, 35 μmol, 10 mol % Pd) was added to chloride 3 (113 mg, 353 μmol) in ethanol:dichloromethane (3:1, 4.0 mL). The mixture was degassed and placed under H2 (1 atm) and stirred for 1 h. The mixture, filtered through a 0.45 μm syringe filter and concentrated under reduced pressure provided 4 (98.1 mg, 96%) as a solid: LRESIMS m/z 289.4 [M+H]+, calcd. for C12H9Cl1F3N2O1 289.0.

Workup

  1. customThe mixture was degassed
  2. filtrationThe mixture, filtered through a 0.45 μm syringe
  3. filtrationfilter
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-27138aec85e849e382c75bbd1e410b6b
Source dataset
uspto-grants-2013_10
Patent number
US08546403B2

Reaction notes

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