Water → N-[2-(3-chloro-5-methoxypyridin-2-yl)-2-oxoethyl]phthalimide

HRID 56006Notes

Reaction equation

Br[CH2:2][C:3]([C:5]1[C:10]([Cl:11])=[CH:9][C:8]([O:12][CH3:13])=[CH:7][N:6]=1)=[O:4].[C:14]1(=[O:24])[NH:18][C:17](=[O:19])[C:16]2=[CH:20][CH:21]=[CH:22][CH:23]=[C:15]12.[K].[I-].[K+].O>CN(C)C=O>[Cl:11][C:10]1[C:5]([C:3](=[O:4])[CH2:2][N:18]2[C:17](=[O:19])[C:16]3=[CH:20][CH:21]=[CH:22][CH:23]=[C:15]3[C:14]2=[O:24])=[N:6][CH:7]=[C:8]([O:12][CH3:13])[CH:9]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To 570 mg of 2-bromo-1-(3-chloro-5-methoxypyridin-2-yl)ethanone in 10 ml of N,N-dimethylformamide, 800 mg of potassium phthalimide and 36 mg of potassium iodide were added, and the mixture was stirred at 80° C. for 5 hours. After completion of the reaction, the reaction mixture was allowed to cool to room temperature, mixed with 20 ml of water and extracted with ethyl acetate (40 ml×1), the resulting organic layer was dried over saturated aqueous sodium chloride and then anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography using ethyl acetate-hexane (with a gradient of from 1:9 to 3:7) as the eluent to obtain 0.12 g of the desired product as white crystals.

Workup

customAfter completion of the reaction
temperatureto cool to room temperature
extractionextracted with ethyl acetate (40 ml×1)
dry with materialthe resulting organic layer was dried over saturated aqueous sodium chloride
customanhydrous sodium sulfate, and the solvent was evaporated under reduced pressure
customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-0752310c72014661b16a307e86ac7ed8
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434684B2

Reaction notes

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