Hydrochloric Acid → [3-(4-chlorobenzyl)-4,7-dimethylquinolin-5-yloxy]acetic Acid Methyl Ester

HRID 2266634Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:27])[CH2:4][O:5][C:6]1[CH:15]=[C:14]([CH3:16])[CH:13]=[C:12]2[C:7]=1[C:8]([CH3:26])=[C:9]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=1)[C:10](Cl)=[N:11]2.Cl>[Pd].C(O)C>[CH3:1][O:2][C:3](=[O:27])[CH2:4][O:5][C:6]1[CH:15]=[C:14]([CH3:16])[CH:13]=[C:12]2[C:7]=1[C:8]([CH3:26])=[C:9]([CH2:18][C:19]1[CH:20]=[CH:21][C:22]([Cl:25])=[CH:23][CH:24]=1)[CH:10]=[N:11]2

Participants

Conditions

Temperature: 40 °C

Procedure

A mixture of [2-chloro-3-(4-chlorobenzyl)-4,7-dimethylquinolin-5-yloxy]acetic acid methyl ester (0.20 g), palladium (10 wt. % on activated carbon, 0.020 g), ethanol (7.0 mL) and 1.0 M aqueous hydrochloric acid (1.5 mL) was stirred at 40° C. for 17 hours under an atmosphere of hydrogen. The mixture was filtered through hyflo, washed with ethanol and the filtrate concentrated under reduced pressure to afford title compound, 0.18 g.

Workup

filtrationThe mixture was filtered through hyflo
washwashed with ethanol
concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record: ord-d79f11246e754723bc265eecaede84c9
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07858640B2

Reaction notes

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