Potassium trimethylsilanolate → [3-(4-chlorobenzyl)-4,7-dimethylquinolin-5-yloxy]acetic Acid

HRID 2266635Notes

Reaction equation

C[O:2][C:3](=[O:26])[CH2:4][O:5][C:6]1[CH:15]=[C:14]([CH3:16])[CH:13]=[C:12]2[C:7]=1[C:8]([CH3:25])=[C:9]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=1)[CH:10]=[N:11]2.C[Si](C)(C)[O-].[K+]>O1CCCC1>[Cl:24][C:21]1[CH:20]=[CH:19][C:18]([CH2:17][C:9]2[CH:10]=[N:11][C:12]3[C:7]([C:8]=2[CH3:25])=[C:6]([O:5][CH2:4][C:3]([OH:26])=[O:2])[CH:15]=[C:14]([CH3:16])[CH:13]=3)=[CH:23][CH:22]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of [3-(4-chlorobenzyl)-4,7-dimethylquinolin-5-yloxy]acetic acid methyl ester (1.8 g), tetrahydrofuran and potassium trimethylsilanolate (0.19 g) was heated at 100° C. in a microwave reactor for 5 minutes. The mixture was concentrated under reduced pressure, diluted with water and acidified by the addition of concentrated hydrochloric acid. The resulting precipitate was collected by filtration and purified by preparative reverse-phase HPLC, using a gradient over 30 minutes of acetonitrile in water (35% to 95% organic modifier) to afford title compound, 0.015 g.

Workup

concentrationThe mixture was concentrated under reduced pressure
additiondiluted with water
additionacidified by the addition of concentrated hydrochloric acid
filtrationThe resulting precipitate was collected by filtration
custompurified by preparative reverse-phase HPLC
customover 30 minutes

Sources & evidence

ORD record: ord-498f70889cdf42a89140fb26f29ca368
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07858640B2

Reaction notes

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