Dimethylformamide → HCID 68779513, compound

HRID 2266607Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:22])=[C:6]2[C:11]=1[NH:10][C:9](=[O:12])[C:8]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=1)=[C:7]2[CH3:21].CN(C)C=O.[H-].[Na+].[CH3:30][O:31][C:32](=[O:37])[C:33](Br)([CH3:35])[CH3:34]>O>[CH3:30][O:31][C:32](=[O:37])[C:33]([O:22][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[C:11]2[C:6]=1[C:7]([CH3:21])=[C:8]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=1)[C:9](=[O:12])[NH:10]2)([CH3:35])[CH3:34]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 8-chloro-3-(4-chlorobenzyl)-5-hydroxy-4-methyl-1H-quinolin-2-one (0.14 g), N,N-dimethylformamide (10 mL), sodium hydride (60% in oil, 0.020 g) and 2-bromo-2-methylpropionic acid methyl ester (0.11 g) was stirred at 100° C. for 3 days. The mixture was cooled to room temperature, diluted with water and extracted with ethyl acetate. The combined extracts were dried over magnesium sulfate and the solvent removed under reduced pressure. The residue was purified by column chromatography on silica gel, eluting with a mixture of ethyl acetate and cyclohexane (3:7 by volume) to afford title compound, 0.056 g.

Workup

temperatureThe mixture was cooled to room temperature
extractionextracted with ethyl acetate
dry with materialThe combined extracts were dried over magnesium sulfate
customthe solvent removed under reduced pressure
customThe residue was purified by column chromatography on silica gel
washeluting with a mixture of ethyl acetate and cyclohexane (3:7 by volume)

Sources & evidence

ORD record: ord-e8fbf7c2b4d94ab0b9eae898b62436e8
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07858640B2

Reaction notes

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