Pyridine, 4-(4-nitrophenoxy)-2-(trifluoromethyl)- → 4-{[2-(Trifluoromethyl)pyridin-4-yl]oxy}aniline

HRID 1993541Notes

Reaction equation

HRID 1993541 reaction equation
[N+:1]([C:4]1[CH:20]=[CH:19][C:7]([O:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=2)=[CH:6][CH:5]=1)([O-])=O>[Ni].CO>[F:18][C:15]([F:16])([F:17])[C:11]1[CH:10]=[C:9]([O:8][C:7]2[CH:19]=[CH:20][C:4]([NH2:1])=[CH:5][CH:6]=2)[CH:14]=[CH:13][N:12]=1

Participants

4

Reactant 1

HCID 68538059Pyridine, 4-(4-nitrophenoxy)-2-(trifluoromethyl)-

Product 1

HCID 591345604-{[2-(Trifluoromethyl)pyridin-4-yl]oxy}aniline

Reagents, catalysts & solvents 2

HCID 935NickelCatalyst2×HCID 887MethanolSolvent

Procedure

A suspension of 4-(4-nitro-phenoxy)-2-trifluoromethyl-pyridine (1.16 g, 4.08 mmol) and Raney Nickel (0.4 9, in EtOH) in MeOH (70 mL) is stirred at rt and under a hydrogen atmosphere for 7 h. Additional Raney Nickel (tip of spatula) is then added and the reaction mixture is stirred for 17 h. The mixture is filtered through a pad of celite and the filter cake is washed with copious amount of MeOH. After removal of the solvents in vacuo, the residue is purified by silica gel (50 g) column chromatography (CH2Cl2/Et2O, 95/5) to afford the title compound as a white solid: ES-MS: 255.0 [M+H]+; single peak at tR=5.97 min (System 2); Rf=0.40 (CH2Cl2/Et2O, 90/10).

Workup

  1. stirringthe reaction mixture is stirred for 17 h
  2. filtrationThe mixture is filtered through a pad of celite
  3. washthe filter cake is washed with copious amount of MeOH
  4. customAfter removal of the solvents in vacuo
  5. customthe residue is purified by silica gel (50 g) column chromatography (CH2Cl2/Et2O, 95/5)

Sources & evidence

ORD record
ord-b9d9aa476afd4689977a63004f27e096
Source dataset
uspto-grants-2010_01
Patent number
US07652022B2

Reaction notes

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