Lithium Hydroxide → 2-[8-chloro-3-(4-chlorobenzyl)-2,4-dimethylquinolin-5-yloxy]propionic Acid

HRID 2266498Notes

Reaction equation

HRID 2266498 reaction equation
C[O:2][C:3](=[O:28])[CH:4]([O:6][C:7]1[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]2[C:8]=1[C:9]([CH3:27])=[C:10]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=1)[C:11]([CH3:18])=[N:12]2)[CH3:5].[OH-].[Li+]>O1CCCC1>[Cl:17][C:14]1[CH:15]=[CH:16][C:7]([O:6][CH:4]([CH3:5])[C:3]([OH:28])=[O:2])=[C:8]2[C:13]=1[N:12]=[C:11]([CH3:18])[C:10]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=1)=[C:9]2[CH3:27]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 687793962-[8-chloro-3-(4-chlorobenzyl)-2,4-dimethylquinolin-5-yloxy]propionic Acid Methyl Ester

Product 1

HCID 577425022-[8-chloro-3-(4-chlorobenzyl)-2,4-dimethylquinolin-5-yloxy]propionic Acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-[8-chloro-3-(4-chlorobenzyl)-2,4-dimethylquinolin-5-yloxy]propionic acid methyl ester (0.092 g), tetrahydrofuran (2.0 mL) and 1.0 M aqueous lithium hydroxide solution (0.25 mL) was stirred at room temperature for 30 minutes. The tetrahydrofuran was removed under reduced pressure and pH of the residue was adjusted to 2 by the addition of 1.0 M aqueous hydrochloric acid. The mixture was extracted with ethyl acetate and the combined extracts washed with saturated aqueous sodium chloride solution and dried over magnesium sulfate. The solvent was removed under reduced pressure and the resulting solid washed with pentane to afford title compound, 0.080 g.

Workup

  1. customThe tetrahydrofuran was removed under reduced pressure and pH of the residue
  2. additionwas adjusted to 2 by the addition of 1.0 M aqueous hydrochloric acid
  3. extractionThe mixture was extracted with ethyl acetate
  4. washthe combined extracts washed with saturated aqueous sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was removed under reduced pressure
  7. washthe resulting solid washed with pentane

Sources & evidence

ORD record
ord-ed5c47b5ef634f6eac3007fb7b242183
Source dataset
uspto-grants-2010_12
Patent number
US07858640B2

Reaction notes

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