Pyridine → N-[2-(3-chloro-5-methoxypyridin-2-yl)-2-(methoxyimino)ethyl]phthalimide

HRID 56007Notes

Reaction equation

[Cl:1][C:2]1[C:3]([C:10](=O)[CH2:11][N:12]2[C:16](=[O:17])[C:15]3=[CH:18][CH:19]=[CH:20][CH:21]=[C:14]3[C:13]2=[O:22])=[N:4][CH:5]=[C:6]([O:8][CH3:9])[CH:7]=1.Cl.[CH3:25][O:26][NH2:27].N1C=CC=CC=1>C(O)C>[Cl:1][C:2]1[C:3]([C:10](=[N:27][O:26][CH3:25])[CH2:11][N:12]2[C:16](=[O:17])[C:15]3=[CH:18][CH:19]=[CH:20][CH:21]=[C:14]3[C:13]2=[O:22])=[N:4][CH:5]=[C:6]([O:8][CH3:9])[CH:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 120 mg of N-[2-(3-chloro-5-methoxypyridin-2-yl)-2-oxoethyl]phthalimide and 60 mg of methoxyamine hydrochloride in 5 ml of ethanol, 85 mg of pyridine was added, and the mixture was stirred at 80° C. for 6 hours. After completion of the reaction, the solvent was evaporated under reduced pressure, and 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 101 mg of the desired product as a pale yellow oil.

Workup

customAfter completion of the reaction
customthe solvent was evaporated under reduced pressure
customthe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-8ff164ffe31f464f9c10a56e47060d9f
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434684B2

Reaction notes

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