Water → HCID 136987055, compound

HRID 55992Notes

Reaction equation

HRID 55992 reaction equation
[Cl:1][C:2]1[C:3]([C:12](=O)[CH2:13][N:14]2[C:18](=[O:19])[C:17]3=[CH:20][CH:21]=[CH:22][CH:23]=[C:16]3[C:15]2=[O:24])=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.Cl.[NH2:27][OH:28].N1C=CC=CC=1.O>C(O)C>[Cl:1][C:2]1[C:3]([C:12](=[N:27][OH:28])[CH2:13][N:14]2[C:18](=[O:19])[C:17]3=[CH:20][CH:21]=[CH:22][CH:23]=[C:16]3[C:15]2=[O:24])=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 66798033N-[2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-2-oxoethyl]phthalimide

Product 1

HCID 136987055HCID 136987055, compoundYield 66.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 0.47 g of N-[2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-2-oxoethyl]phthalimide and 0.54 g of hydroxylamine hydrochloride in 5 ml of ethanol, 0.94 g of pyridine was added, and the mixture was stirred at room temperature for 24 hours. After completion of the reaction, the reaction mixture was mixed with 5 ml of water and extracted with ethyl acetate (5 ml×3), the resulting organic layers were combined, dried over saturated aqueous sodium chloride and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resulting residue was purified by preparative medium pressure liquid chromatography (preparative medium pressure chromatograph: YFLC-Wprep manufactured by Yamazen Science, Inc.) using ethyl acetate-hexane (with a gradient of from 1:3 to 2:2) as the eluent to obtain 325 mg of the desired product as white crystals.

Workup

  1. customAfter completion of the reaction
  2. extractionextracted with ethyl acetate (5 ml×3)
  3. dry with materialdried over saturated aqueous sodium chloride
  4. distillationanhydrous sodium sulfate, and the solvent was distilled off under reduced pressure
  5. customThe resulting residue was purified by preparative medium pressure liquid chromatography (preparative medium pressure chromatograph: YFLC-Wprep manufactured by Yamazen Science, Inc.)

Sources & evidence

ORD record
ord-b84814d643454ccf890e9af40f24cc8a
Source dataset
uspto-grants-2016_09
Patent number
US09434684B2

Reaction notes

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