1-(2-Fluoropyridin-4-yl)-2-(3-trifluoromethylphenyl)ethane-1,2-dione-1-oxime → 2-Amino-2-(2-fluoropyridine-4-yl)-1-(3-trifluoromethylphenyl)ethanol

HRID 1596177Notes

Reaction equation

HRID 1596177 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([C:8](=[N:21]O)[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=2)=[O:10])[CH:5]=[CH:4][N:3]=1>[Pd].C(O)C>[NH2:21][CH:8]([C:6]1[CH:5]=[CH:4][N:3]=[C:2]([F:1])[CH:7]=1)[CH:9]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:18])([F:19])[F:20])[CH:12]=1)[OH:10]

Participants

4

Reactant 1

HCID 1363810621-(2-Fluoropyridin-4-yl)-2-(3-trifluoromethylphenyl)ethane-1,2-dione-1-oxime

Product 1

HCID 155242512-Amino-2-(2-fluoropyridine-4-yl)-1-(3-trifluoromethylphenyl)ethanolYield 91.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

10% Palladium on carbon (3.0 g) was added to a solution of 1-(2-fluoropyridin4yl)-2-(3-trifluoromethylphenyl)-ethane-1,2-dione 1-oxime (8.0 g, 27 mmol) in ethanol (400 mL) at ambient temperature. The reaction vessel was vacuum purged, refilled with hydrogen and vigorously stirred for 10 hrs. After the reaction was complete, the solution was filtered through a pad of celite, and concentrated to give a solid. The residue was purified by recrystallization from methylene chloride and hexane to give 7.4 g of the title compound. m.p. 128-129° C.

Workup

  1. custompurged
  2. additionrefilled with hydrogen
  3. filtrationthe solution was filtered through a pad of celite
  4. concentrationconcentrated
  5. customto give a solid
  6. customThe residue was purified by recrystallization from methylene chloride and hexane

Sources & evidence

ORD record
ord-92c25dffda634cbfa4b82efe33d507c4
Source dataset
uspto-grants-2001_09
Patent number
US06291457B1

Reaction notes

Loading…