6-bromo-N-methoxy-N-methylquinoline-2-carboxamide → 1-(6-Bromoquinolin-2-yl)ethanone

HRID 1693071Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12](N(OC)C)=[O:13])[CH:6]=[CH:5]2.[CH3:18][Mg]Br>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12](=[O:13])[CH3:18])[CH:6]=[CH:5]2

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 6-bromo-N-methoxy-N-methylquinoline-2-carboxamide (4.29 g, 14.5 mmol) in THF (100 ml) was added methyl magnesiumbromide (18.2 ml, 17.4 mmol, 0.96M in THF solution) at 0° C. dropwise and the mixture was stirred at 0° C. for 1 hour. Then, the mixture was quenched with saturated ammonium chloride aqueous solution (50 ml) and water (200 ml). After stirring for 30 min, the product was extracted with ethyl acetate which was dried over sodium sulfate. Then, filtration, evaporation and purification through silica gel column chromatography, eluting with hexane/ethyl acetate (4:1), furnished the title compound (3.47 g, 96% yield) as a white solid. 1H NMR (300 MHz, CDCl3) δ 2.66 (3H, s), 7.83-7.88 (1H, m), 8.02-8.20 (4H, m). MS (ESI): m/z 250, 252 (M+H)+.

Workup

customThen, the mixture was quenched with saturated ammonium chloride aqueous solution (50 ml) and water (200 ml)
stirringAfter stirring for 30 min
extractionthe product was extracted with ethyl acetate which
dry with materialwas dried over sodium sulfate
filtrationThen, filtration, evaporation and purification through silica gel column chromatography
washeluting with hexane/ethyl acetate (4:1)

Sources & evidence

ORD record: ord-5c2f439e379a49cfbcc06e98510a5a17
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08158650B2

Reaction notes

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