Pyridine → HCID 117839903, compound

HRID 1520294Notes

Reaction equation

HRID 1520294 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]([C:14](=O)[CH2:15][CH2:16][C:17]([F:20])([F:19])[F:18])=[N:12][CH:13]=2)=[CH:4][CH:3]=1.Cl.[CH3:23][O:24][NH2:25].N1C=CC=CC=1>O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]([C:14](=[N:25][O:24][CH3:23])[CH2:15][CH2:16][C:17]([F:20])([F:19])[F:18])=[N:12][CH:13]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 521874O-Methylhydroxylamine hydrochlorideHCID 117840293HCID 117840293, compound

Product 1

HCID 117839903HCID 117839903, compoundYield 93.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1-(5-(4-chlorophenyl)pyridin-2-yl)-4,4,4-trifluorobutan-1-one (821.7 mg), O-methylhydroxylamine hydrochloride (656 mg) and pyridine (5.239 mL) was stirred at room temperature overnight, and water was added. The mixture was extracted with ethyl acetate, and the extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (842.7 mg).

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washthe extract was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-0ce51e441da4459289424b5e18e0dfe8
Source dataset
uspto-grants-2015_07
Patent number
US09073864B2

Reaction notes

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