Methanesulfonic Acid → 8-chloro-5-hydroxy-3-(4-methanesulfonylbenzyl)-4-methyl-1H-quinolin-2-one

HRID 2266501Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[NH:9][C:10](=[O:26])[CH:11]([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:18][CH:17]=1)[C:12](=O)[CH3:13].CS(O)(=O)=O>C([O-])(=O)C.[Na+]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]2[C:3]=1[NH:9][C:10](=[O:26])[C:11]([CH2:15][C:16]1[CH:17]=[CH:18][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:20][CH:21]=1)=[C:12]2[CH3:13]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of N-(2-chloro-5-hydroxyphenyl)-2-(4-methanesulfonylbenzyl)-3-oxo-butyramide (0.25 g) and methanesulfonic acid (1.1 g) was heated at 100° C. for 10 minutes. The mixture cooled to room temperature and poured into a saturated aqueous solution of sodium acetate (20 mL). The resulting precipitate was collected by filtration, washed with water and dried to afford title compound as a pale pink solid, 0.21 g.

Workup

temperatureThe mixture cooled to room temperature
filtrationThe resulting precipitate was collected by filtration
washwashed with water
customdried

Sources & evidence

ORD record: ord-c3b35f5ecd144c3199fae07c69245444
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07858640B2

Reaction notes

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